Vacation Rentals & Villas in St. Michaels

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72 villas

(3) Very Good 

    15

    Halos'Haven Vacation Rental

    St. Michaels / McDaniel

    McDaniel house

    5 10 2 nights min

    • 5 bedrooms
    • sleeps 10
    • 2 nights min
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $802

    Price per night from

    $802

    (11) Very Good 

      30

      Large Historic Thomas Harrison House on Harbor in St. Michaels Town

      Talbot County / St. Michaels

      St. Michaels house

      7 9 min stay varies

      • 7 bedrooms
      • sleeps 9
      • min stay varies
      • Beach / lakeside relaxation
      • Child Friendly
      • Air conditioning
      “Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that
      …see more

      Price per night from

      $401

      Responds fast!
      avg. 2 hours 48 minutes

      Price per night from

      $401

        18

        Historic Waterfront Property with Wi-Fi and Dock

        Talbot County / St. Michaels

        St. Michaels house

        3 8 2 nights min

        • 3 bedrooms
        • sleeps 8
        • 2 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $859

        Responds fast!
        avg. 3 hours 23 minutes

        Price per night from

        $859

        (24) Excellent 

          27

          Location Location! St Michaels-- In Town Cottage!

          Talbot County / St. Michaels

          St. Michaels house

          2 5 min stay varies

          • 2 bedrooms
          • sleeps 5
          • min stay varies
          • Beach / lakeside relaxation
          • Child Friendly
          • Car not necessary

          Price per night from

          $207

          Responds fast!
          avg. 2 hours 48 minutes

          Price per night from

          $207

          (13) Excellent 

            24

            Premier Cottage in St. Michaels- In Town Location!

            Talbot County / St. Michaels

            St. Michaels house

            2 5 min stay varies

            • 2 bedrooms
            • sleeps 5
            • min stay varies
            • Child Friendly
            • Air conditioning
            • Pet Friendly

            Price per night from

            $207

            Responds fast!
            avg. 2 hours 48 minutes

            Price per night from

            $207

            (3) Excellent 

              24

              Best sunrise in St. Michaels....Broadview Bay House

              Talbot County / St. Michaels

              St. Michaels house

              6 12 min stay varies

              • 6 bedrooms
              • sleeps 12
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $600

              Price per night from

              $600

              (2) Excellent 

                18

                Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

                Talbot County / St. Michaels

                St. Michaels house

                1 6 2 nights min

                • 1 bedroom
                • sleeps 6
                • 2 nights min
                • Child Friendly
                • Air conditioning
                • Private garden

                Price per night from

                $263

                Price per night from

                $263

                (2) Excellent 

                  12

                  Pot Pie House

                  Talbot County / St. Michaels

                  St. Michaels house

                  3 6 3 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 3 nights min
                  • Air conditioning

                  Price per night from

                  $258

                  Price per night from

                  $258

                  (7) Very Good 

                    23

                    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

                    Talbot County / St. Michaels

                    St. Michaels cottage

                    2 5 min stay varies

                    • 2 bedrooms
                    • sleeps 5
                    • min stay varies
                    • Child Friendly
                    • Air conditioning
                    • Pet Friendly

                    Price per night from

                    $218

                    Responds fast!
                    avg. 2 hours 48 minutes

                    Price per night from

                    $218

                    (3) Very Good 

                      25

                      Waterview Cottage In St. Michaels!

                      Talbot County / St. Michaels

                      St. Michaels cottage

                      2 5 min stay varies

                      • 2 bedrooms
                      • sleeps 5
                      • min stay varies
                      • Child Friendly
                      • Air conditioning
                      • Pet Friendly

                      Price per night from

                      $218

                      Responds fast!
                      avg. 2 hours 48 minutes

                      Price per night from

                      $218

                      (5) Excellent 

                        22

                        Sandy Pines: Enjoy Harris Creek w/Pool and Boats

                        Talbot County / St. Michaels

                        St. Michaels house

                        4 10 min stay varies

                        • 4 bedrooms
                        • sleeps 10
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $430

                        Price per night from

                        $430

                          14

                          Halo's Haven Guest Quarters

                          Talbot County / St. Michaels

                          St. Michaels house

                          3 6 1 night min

                          • 3 bedrooms
                          • sleeps 6
                          • 1 night min
                          • Child Friendly
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $373

                          Price per night from

                          $373

                            12

                            Harris Cove Cottages LLC

                            Talbot County / St. Michaels

                            St. Michaels cottage

                            1 4 1 night min

                            • 1 bedroom
                            • sleeps 4
                            • 1 night min
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $229

                            Price per night from

                            $229

                              7

                              St. Michael's Premier in Town Summer Cottage!

                              Talbot County / St. Michaels

                              St. Michaels house

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Child Friendly
                              • Air conditioning
                              • Private garden

                              Price per night from

                              $327

                              Price per night from

                              $327

                              (1) Average 

                                38

                                St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

                                Talbot County / St. Michaels

                                St. Michaels villa

                                6 12 2 nights min

                                • 6 bedrooms
                                • sleeps 12
                                • 2 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 7 mi
                                • Swimming pool

                                Price per night from

                                $1,145

                                Responds fast!
                                avg. 3 hours 35 minutes

                                Price per night from

                                $1,145

                                Great rentals within 20 miles that match your search

                                Distance approx 16.58 km from St. Michaels

                                  26

                                  Love Point Luxury Waterfront in Stevensville

                                  Kent Island / Stevensville

                                  Stevensville house

                                  3 10 3 nights min

                                  • 3 bedrooms
                                  • sleeps 10
                                  • 3 nights min
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $1,602

                                  Price per night from

                                  $1,602

                                  Distance approx 16.12 km from St. Michaels

                                    42

                                    Waterfront Room Rentals 2 with Private Beach

                                    Talbot County / Trappe

                                    Trappe room

                                    1 2 min stay varies

                                    • 1 bedroom
                                    • sleeps 2
                                    • min stay varies
                                    • Child Friendly
                                    • Air conditioning
                                    • Pet Friendly

                                    Price per night from

                                    $115

                                    Responds fast!
                                    avg. 1 hour 34 minutes

                                    Price per night from

                                    $115

                                    Distance approx 16.12 km from St. Michaels

                                      44

                                      Waterfront Room Rentals 3 with Private Beach

                                      Talbot County / Trappe

                                      Trappe room

                                      1 2 min stay varies

                                      • 1 bedroom
                                      • sleeps 2
                                      • min stay varies
                                      • Child Friendly
                                      • Air conditioning
                                      • Pet Friendly

                                      Price per night from

                                      $115

                                      Responds fast!
                                      avg. 1 hour 34 minutes

                                      Price per night from

                                      $115

                                      Distance approx 3.11 km from St. Michaels Show on Map

                                        37

                                        St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

                                        Talbot County / Royal Oak

                                        Royal Oak house

                                        5 10 min stay varies

                                        • 5 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $572

                                        Price per night from

                                        $572

                                        Distance approx 19.23 km from St. Michaels

                                          24

                                          NEW! Annapolis Home w/ Deck & Whitehall Bay Access

                                          Maryland / Cape Saint Claire

                                          Cape Saint Claire house

                                          4 8 min stay varies

                                          • 4 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $251

                                          Responds fast!
                                          avg. 9 minutes

                                          Price per night from

                                          $251

                                          Distance approx 10.43 km from St. Michaels

                                            25

                                            Waterfront Stevensville House w/ Pier & 2 Decks!

                                            Kent Island / Stevensville

                                            Stevensville house

                                            5 12 min stay varies

                                            • 5 bedrooms
                                            • sleeps 12
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $487

                                            Responds fast!
                                            avg. 9 minutes

                                            Price per night from

                                            $487

                                            Distance approx 15.75 km from St. Michaels

                                              26

                                              Annapolis Crows Nest Cottage: Chesapeake Bay View

                                              Maryland / Annapolis

                                              Annapolis villa

                                              5 20 min stay varies

                                              • 5 bedrooms
                                              • sleeps 20
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.2 mi
                                              • Child Friendly

                                              Price per night from

                                              $796

                                              Price per night from

                                              $796

                                              Distance approx 17.89 km from St. Michaels

                                                8

                                                6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

                                                Maryland / Cambridge

                                                Cambridge house

                                                6 12 3 nights min

                                                • 6 bedrooms
                                                • sleeps 12
                                                • 3 nights min
                                                • Child Friendly
                                                • Air conditioning
                                                • Pet Friendly

                                                Price per night from

                                                $995

                                                Price per night from

                                                $995

                                                Distance approx 5.32 km from St. Michaels Show on Map

                                                  28

                                                  St. Michaels Area Cottage - Walk to Water & Marina

                                                  Talbot County / Neavitt

                                                  Neavitt house

                                                  2 4 2 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 2 nights min
                                                  • Child Friendly
                                                  • Air conditioning
                                                  • Pet Friendly

                                                  Price per night from

                                                  $212

                                                  Responds fast!
                                                  avg. 9 minutes

                                                  Price per night from

                                                  $212

                                                  Distance approx 17.55 km from St. Michaels

                                                    11

                                                    Panoramic Views of Herrington Harbour on the Bay.

                                                    Calvert County / North Beach

                                                    North Beach house

                                                    3 8 1 night min

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • 1 night min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Pet Friendly

                                                    Price per night from

                                                    $573

                                                    Price per night from

                                                    $573

                                                    Distance approx 5.19 km from St. Michaels Show on Map

                                                    (1) Excellent 

                                                      9

                                                      Cottage 2 at Grandview Pleasure Point

                                                      Talbot County / Bozman

                                                      Bozman house

                                                      2 6 2 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 2 nights min
                                                      • Beach / lakeside relaxation
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $442

                                                      Price per night from

                                                      $442

                                                      Distance approx 17.41 km from St. Michaels

                                                      (12) Very Good 

                                                        31

                                                        Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

                                                        Maryland / Cambridge

                                                        Cambridge house

                                                        6 20 min stay varies

                                                        • 6 bedrooms
                                                        • sleeps 20
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 0.1 mi
                                                        • Swimming pool
                                                        “Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle
                                                        …see more

                                                        Price per night from

                                                        $572

                                                        Price per night from

                                                        $572

                                                        Distance approx 16.55 km from St. Michaels

                                                          11

                                                          Love Point Bay Vacation Home

                                                          Kent Island / Stevensville

                                                          Stevensville apartment

                                                          2 6 2 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 2 nights min
                                                          • Child Friendly

                                                          Price per night from

                                                          $377

                                                          Price per night from

                                                          $377

                                                          Distance approx 17.96 km from St. Michaels

                                                          (14) Excellent 

                                                            19

                                                            Love Point Waterfront

                                                            Maryland / Kent Island

                                                            Kent Island house

                                                            3 12 3 nights min

                                                            • 3 bedrooms
                                                            • sleeps 12
                                                            • 3 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 5 mi
                                                            • Child Friendly
                                                            “Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans
                                                            …see more

                                                            Price per night from

                                                            $287

                                                            Price per night from

                                                            $287

                                                            Distance approx 18.91 km from St. Michaels

                                                              15

                                                              Location,location,location,walk to city dock,free

                                                              Maryland / Annapolis

                                                              Annapolis apartment

                                                              2 5 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • min stay varies
                                                              • Car not necessary
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $287

                                                              Price per night from

                                                              $287

                                                              Distance approx 17.32 km from St. Michaels

                                                                17

                                                                Deerpond Carriage House

                                                                Maryland / Woolford

                                                                Woolford guest house

                                                                1 2 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 3 nights min
                                                                • Swimming pool
                                                                • Air conditioning
                                                                • Private garden

                                                                Price per night from

                                                                $207

                                                                Price per night from

                                                                $207

                                                                Distance approx 19.67 km from St. Michaels

                                                                (1) Excellent 

                                                                  18

                                                                  Stunning Home in the Heart of Downtown Annapolis

                                                                  Maryland / Annapolis

                                                                  Annapolis house

                                                                  3 11 2 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 11
                                                                  • 2 nights min
                                                                  • Ask about children
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $796

                                                                  Price per night from

                                                                  $796

                                                                  Distance approx 16.33 km from St. Michaels

                                                                    39

                                                                    Annapolis Home w/ Bay Views - Near Naval Academy!

                                                                    Maryland / Annapolis

                                                                    Annapolis house

                                                                    5 11 min stay varies

                                                                    • 5 bedrooms
                                                                    • sleeps 11
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $819

                                                                    Responds fast!
                                                                    avg. 9 minutes

                                                                    Price per night from

                                                                    $819

                                                                    Distance approx 16.31 km from St. Michaels

                                                                    (2)  

                                                                      26

                                                                      3BR Annapolis Home on Oyster Creek w/Amazing Views

                                                                      Maryland / Annapolis

                                                                      Annapolis house

                                                                      3 9 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 9
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $401

                                                                      Responds fast!
                                                                      avg. 9 minutes

                                                                      Price per night from

                                                                      $401

                                                                      Distance approx 11.05 km from St. Michaels

                                                                      (1) Excellent 

                                                                        32

                                                                        KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

                                                                        Maryland / Kent Island

                                                                        Kent Island house

                                                                        4 10 2 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 10
                                                                        • 2 nights min
                                                                        • Nearest beach 5 mi
                                                                        • Swimming pool
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $1,718

                                                                        Price per night from

                                                                        $1,718

                                                                        Distance approx 13.2 km from St. Michaels

                                                                        (15) Excellent 

                                                                          35

                                                                          Luxury vacation condominum with private beach

                                                                          Kent Island / Chester

                                                                          Chester house

                                                                          4 10 2 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • 2 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 0.2 mi
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $440

                                                                          Price per night from

                                                                          $440

                                                                          Distance approx 3.66 km from St. Michaels Show on Map

                                                                          (10) Excellent 

                                                                            24

                                                                            RESTORED WATERFRONT COTTAGE

                                                                            Talbot County / Royal Oak

                                                                            Royal Oak cottage

                                                                            3 6 2 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 2 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $344

                                                                            Price per night from

                                                                            $344

                                                                            Distance approx 11.36 km from St. Michaels

                                                                            (5) Excellent 

                                                                              17

                                                                              KI Golf House-A PAR for the Course & Mile to Beach

                                                                              Maryland / Kent Island

                                                                              Kent Island house

                                                                              4 10 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Nearest beach 1 mi
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $458

                                                                              Responds fast!
                                                                              avg. 1 hour 7 minutes

                                                                              Price per night from

                                                                              $458

                                                                              About St. Michaels

                                                                              St. Michaels has been a popular vacation destination for years – find out why by booking your vacation rental with FlipKey, today!

                                                                              About St. Michaels, Maryland

                                                                              This small town in Talbot County is famous throughout the east coast for being the perfect getaway spot.

                                                                              It's slightly unusual, as it wasn't built in a grid form like so many other American towns. Instead, it centers around the town square and progresses outwards in layers.

                                                                              Way back in the past, it was a tobacco growing and shipbuilding town. A real taste of old-time Americana. But, now its trade focuses on tourism and oysters – the latter are always delicious and well worth trying during your stay.

                                                                              Plans to improve the town have been underway since the 60s. There's now a museum, waterfront restaurants and tour boats that make it a much more exciting place to stay. Check them out for yourself when you come here.

                                                                              You may recognize this small town as it's starred in a few movies. Clara's Heart (starring Whoopi Goldberg and Neil Patrick Harris), and The Wedding Crashers (with Owen Wilson and Vince Vaughn) were both filmed here – how about that for a bit of Hollywood glitz and glamour?

                                                                              What to do

                                                                              FIrst stop, go to the Chesapeake Bay Maritime Museum. It's a really interesting place for sailing enthusiasts and history nuts. The exhibits are mostly historic bay vessels, including the ‘Chesapeake Bay bugeye’ named Edna E. Lockwood – ask the guide about that one!

                                                                              For a little more history, go to the St. Michael's Mill. It’s a grist mill that dates back to the 19th century, and was a major part of the town life for the locals of yesteryear.

                                                                              If you want some culture, there are three art galleries to choose from. The Clark Gallery, Hopkins and Gregario – all with something a little different for you to explore.

                                                                              If you're looking for some fun activities to try during your stay, there are plenty. Take a boat out on the water and explore the area. Or, try stand up paddleboarding – it's hard work but great fun!

                                                                              There are several running and kayaking trails for you to discover. Or, you could spend a day fishing in the shallow waters.

                                                                              Top St. Michaels, Maryland travel tips

                                                                              Most of St. Michaels is dog-friendly, so bring your pooch along on vacation and let them explore someplace new.

                                                                              You'll have your pick of riverfront restaurants during your stay. Make sure to try the fresh seafood, but remember to tip as gratuity is not included.

                                                                              For a peaceful trip away by the water, choose St. Michaels as your next vacation destination. Pick your St. Michaels vacation rental on FlipKey and let the adventure begin!