Vacation rentals in Saint Michaels

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Saint Michaels

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Cottage in Saint Michaels
St. Michaels-Historic Dist. Margaret Wells House
The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.
20 – 27 Nov
4.98 out of 5 average rating, 417 reviews
Guest favourite
Guest suite in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.
2 – 9 Aug
4.91 out of 5 average rating, 123 reviews
Guest favourite
Home in Cambridge
"Happy Campers" Waterfront Apartment!
Come and experience a relaxing getaway at our fully furnished, detached waterfront apartment! Happy Campers is located on the Choptank River, surrounded by acres of pristine land! You will enjoy quiet afternoons, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery! A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park!
21 – 28 Aug
5.0 out of 5 average rating, 262 reviews

Popular amenities for Saint Michaels holiday rentals

Stay near Saint Michaels's top sights

Chesapeake Bay Maritime Museum39 locals recommend
Ava's Pizzeria & Wine Bar - St. Michaels20 locals recommend
The Crab Claw11 locals recommend
Foxy's Harbor Grille17 locals recommend
Sail Selina II, St. Michaels6 locals recommend
Carpenter Street Saloon10 locals recommend

Other great holiday rentals in Saint Michaels

Guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
25 Mar – 1 Apr
5.0 out of 5 average rating, 103 reviews
Guest favourite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
24 Nov – 1 Dec
5.0 out of 5 average rating, 111 reviews
Guest favourite
Apartment in Saint Michaels
Blue Crab Lodge
3 – 10 Dec
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Saint Michaels
SM’s Premier Rental Heated Pool opens 4/12
16 – 23 Sept
4.97 out of 5 average rating, 78 reviews
Guest favourite
Home in Saint Michaels
Shipwrights Cottage in Town!
13 – 20 Jan
5.0 out of 5 average rating, 28 reviews
Guest favourite
Cabin in Saint Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
8 – 15 Dec
5.0 out of 5 average rating, 93 reviews
Guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub & Firepit
9 – 16 Dec
5.0 out of 5 average rating, 83 reviews
Guest favourite
Home in Saint Michaels
Waterfront Family Vacation Estate with pool
25 Mar – 1 Apr
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Easton
Tuckaway Cove Relaxing waterfront property
16 – 23 Nov
5.0 out of 5 average rating, 40 reviews
Guest favourite
Guesthouse in Oxford
The Nichols House Cottage
25 Aug – 1 Sept
4.99 out of 5 average rating, 81 reviews
Guest favourite
Barn in Queenstown
Waterfront Modern Guest Barn
24 June – 1 July
5.0 out of 5 average rating, 41 reviews
Guest favourite
Guesthouse in Saint Michaels
The Suite at Mostly Porches
8 – 15 Oct
5.0 out of 5 average rating, 12 reviews

Quick stats about holiday rentals in Saint Michaels

Total rentals

40 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

2.7K reviews

Nightly prices starting at

$152 AUD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Talbot County
  5. Saint Michaels