Vacation Rentals & Villas in St. Michaels

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82 villas

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 29 minutes

Price per night from

$352

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 11 minutes

Price per night from

$859

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 29 minutes

Price per night from

$381

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$716

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$2,289

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,289

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$1,889

Great rentals within 20 miles that match your search

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

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“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, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

Price per night from

$452

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$218

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$321

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$218

Main House at Grandview at Pleasure Point

Bozman house

4 bedrooms / 3 bathrooms / sleeps 9

“Family Fun at Grandview” Our group of grandparents, children with spouses, & grandchildren spent a week in the main house at Grandview. We had a great time in the pool, on the docks, in the porches, & exploring this very large & private property. We also enjoyed the shopping, restaurants, & Maritime Museum in St. Michaels. It was a very hot week & the many fans that were provided made it comfortable. The kitchen was well equipped to handle a large group & we had a great seafood feast on the picnic tables by the pool.

Price per night from

$664

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$1,025

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 46 minutes

Price per night from

$250

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“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, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Price per night from

$458

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$801

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

Kent Island house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$1,946

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,946

Responds fast! avg. 1 hour 2 minutes

Price per night from

$458

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,145

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

$487

Tentrr Signature Site - Wye Island View

Grasonville tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$229

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Neavitt manor house

25 bedrooms / 25 bathrooms / sleeps 50

Price per night from

$8,583

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

8 bedrooms / 10 bathrooms / sleeps 12

Price per night from

$2,861

Cozy cottage with expansive backyard and firepit!

Tracys Landing house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$286

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!

Responds fast! avg. 22 minutes

Price per night from

$1,889

Breathtaking Waterfront Cambridge Getaway

Cambridge house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$681

Cozy Downtown Annapolis Apartment

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$248

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$400

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$6,866

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,116

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,105

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$800

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

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 18

“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 clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

Responds fast! avg. 3 hours 35 minutes

Price per night from

$915

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$458

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$183

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$189

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$573

Viewing 38 of 82
rentals in St. Michaels

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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!

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

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