Vacation Rentals & Villas in St. Michaels

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73 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

$700

Price per night from

$700

(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

$160

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$160

(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

$290

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$290

(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
“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin
…see more

Price per night from

$148

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$148

(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

$229

Price per night from

$229

(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

$225

Price per night from

$225

(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

$596

Price per night from

$596

(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

$150

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$150

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

$745

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$745

(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

$160

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$160

(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

$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

$199

Price per night from

$199

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

$325

Price per night from

$325

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

$283

Price per night from

$283

(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

$839

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$839

Great rentals within 20 miles that match your search

Distance approx 16.31 km from St. Michaels

29

NEW! Colonial Home in Cambridge w/Wraparound Porch

Maryland / Cambridge

Cambridge house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$220

Responds fast!
avg. 12 minutes

Price per night from

$220

Distance approx 16.12 km from St. Michaels

(5) Average 

55

Waterfront Vacation Home with Private Beach

Talbot County / Trappe

Trappe house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Child Friendly

Price per night from

$326

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$326

Distance approx 15.86 km from St. Michaels

16

Choptank River View House

Maryland / Cambridge

Cambridge house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

Price per night from

$993

Price per night from

$993

Distance approx 17.7 km from St. Michaels

(5) Very Good 

17

Seahorse Guest Cottage near the Bay, dog friendly

Calvert County / North Beach

North Beach cottage

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$159

Responds fast!
avg. 12 minutes

Price per night from

$159

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

$686

Price per night from

$686

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

$1,389

Price per night from

$1,389

Distance approx 8.9 km from St. Michaels Show on Map

(1) Excellent 

26

Huge Stevensville House Overlooking Eastern Shore!

Kent Island / Stevensville

Stevensville house

3 10 min stay varies

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

Price per night from

$397

Responds fast!
avg. 9 minutes

Price per night from

$397

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

$373

Responds fast!
avg. 10 minutes

Price per night from

$373

Distance approx 15.05 km from St. Michaels

24

Shady Side House on Chesapeake Bay Near Marina!

Maryland / Shady Side

Shady Side house

2 5 min stay varies

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

Price per night from

$184

Responds fast!
avg. 9 minutes

Price per night from

$184

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

$174

Responds fast!
avg. 12 minutes

Price per night from

$174

Distance approx 5.18 km from St. Michaels Show on Map

8

Cottage 1a at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$244

Price per night from

$244

Distance approx 12.34 km from St. Michaels

(3) Excellent 

21

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Kent Island / Chester

Chester house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 14 mi
  • Child Friendly
“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,
…see more

Price per night from

$283

Price per night from

$283

Distance approx 17.37 km from St. Michaels

9

Renovated Luxury Waterview House

Calvert County / North Beach

North Beach house

3 6 2 nights min

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

Price per night from

$296

Price per night from

$296

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

$383

Price per night from

$383

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

$493

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$493

Distance approx 19.12 km from St. Michaels

(2) Excellent 

52

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Maryland / Annapolis

Annapolis house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 mi
  • Child Friendly
  • Car not necessary

Price per night from

$249

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$249

Distance approx 16.68 km from St. Michaels

43

The Yellow House- Gorgeous Southern Colonial

Maryland / Annapolis

Annapolis house

6 14 4 nights min

  • 6 bedrooms
  • sleeps 14
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$982

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$982

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

$1,489

Price per night from

$1,489

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

$437

Price per night from

$437

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 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$596

Price per night from

$596

Distance approx 11.74 km from St. Michaels

9

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Kent Island / Stevensville

Stevensville house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$645

Price per night from

$645

Distance approx 14.3 km from St. Michaels

(10) Excellent 

50

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Maryland / Cambridge

Cambridge cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$166

Price per night from

$166

Distance approx 16.39 km from St. Michaels

23

EASTERN SHORE MARYLAND WELCOMES YOU

Maryland / Preston

Preston house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$74

Price per night from

$74

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!