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Vacation Rentals & Villas in St. Michaels

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59 villas

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“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 you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

Price per night from

$622

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$259

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

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$207

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 47 minutes

Price per night from

$864

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$334

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$311

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$334

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

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$334

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$793

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$444

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$2,407

Great rentals within 20 miles that match your search

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$654

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Cambridge house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,139

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,310

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$590

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$316

Waterfront Annapolis Area 3BR/3BA Retreat with Private Pier

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 24 minutes

Price per night from

$515

NEW! Classic Family Home: Water View, Walk to Pier

Mayo house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 9 minutes

Price per night from

$212

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 50 minutes

Price per night from

$1,983

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$450

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$286

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite. As for the house itself, we couldn't have asked for more. It is spacious, clean, and has all of the amenities you could want. I must also mention that it was a breeze and a pleasure working with the folks at Grandview. They are incredibly responsive, and make a great effort to ensure that you enjoy your stay.

Price per night from

$804

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$282

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

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$945

Year Round Estate on Bay / Fam. Reunions / Slps 28

Cambridge house

7 bedrooms / 7 bathrooms / sleeps 28

“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was propabaly the most memorable week our family has ever spent together. The house was absolutely perfect! Clean, beautifully furnished, amenities for all ages and the most spectacular grounds and views for the entire family to enjoy. We are already planning our stay for next summer and hope to come back this winter as well for a long weekend. Thank you thank you thank you!

Price per night from

$1,620

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$803

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$329

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$461

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Price per night from

$490

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 39 minutes

Price per night from

$209

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 9 minutes

Price per night from

$293

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 9 minutes

Price per night from

$287

NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

North Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 9 minutes

Price per night from

$90

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$576

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$288

NEW! Chic Condo w/ Balcony 1Mi to Annapolis Harbor

Annapolis condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 9 minutes

Price per night from

$226

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Shady Side house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 7 minutes

Price per night from

$411

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Chesapeake Beach apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 5 minutes

Price per night from

$84

Viewing 38 of 59
rentals in St. Michaels

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About St. Michaels

St. Michaels has been a popular vacation destination for years &ndash; 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 &ndash; 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 &ndash; 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 &lsquo;Chesapeake Bay bugeye&rsquo; named Edna E. Lockwood &ndash; ask the guide about that one!

For a little more history, go to the St. Michael's Mill. It&rsquo;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 &ndash; 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 &ndash; 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!

Top Destination reviews

Location Location! St Michaels-- In Town Cottage!
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 building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable. I have visited this cottage several times and will continue to do so! A great place to gather with family and friends or a quick weekend escape to enjoy life on the shore.see more
Sandy Pines: Enjoy Harris Creek w/Pool and Boats
Perfect weekend getaway!

My family recently spent a memorable weekend in December at Sandy Pines. We comfortably shared the house with a group of friends -- three other couples and their young children. The house has a lovely home-away-from-home feel. We especially enjoyed the wood-burning fireplace in the evenings. Sandy Pines is perfectly situated -- a short drive from St. Michaels, and on a tranquil spot by the Bay. This is an ideal vacation rental for those who wish to enjoy the Eastern Shore to the fullest. I even managed to fit in a kayak ride! We would highly recommend Sandy Pines!see more
Large Historic Thomas Harrison House on Harbor in St. Michaels Town
Bike Trip!

We loved this house and especially the location! Plenty of room for 11 of our friends! We loved the outside area and being right on the water! Walking distance to so many places! Loved it and hope to stay there again next year! … see more

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