Saint Michaels vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Saint Michaels

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

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 418 reviews

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.

Mar 19 – 26

R3,926 ZAR per night
Guest favorite

Apartment in Saint Michaels

4.91 out of 5 average rating, 124 reviews

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.

Aug 22 – 29

R7,535 ZAR per night
Superhost

Home in Cambridge

5.0 out of 5 average rating, 263 reviews

"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!

Mar 8 – 15

R2,929 ZAR per night

Popular amenities for Saint Michaels vacation 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

Saint Michaels house rentals

Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 103 reviews

Historic Downtown in-law suite

Jan 9 – 16

R2,300 ZAR per night
Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Mar 18 – 25

R9,111 ZAR per night
Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 221 reviews

River Front, Private Single Family Home

Dec 22 – 29

R10,152 ZAR per night
Guest favorite

Home in Kent Narrows

5.0 out of 5 average rating, 275 reviews

Chester Riverfront At Kent Narrows

Nov 6 – 13

R7,198 ZAR per night
Guest favorite

Home in Lusby

5.0 out of 5 average rating, 110 reviews

Historic Rousby Hall, Waterfront, Patuxent River

Oct 20 – 27

R14,132 ZAR per night
Guest favorite

Home in St Michaels

4.85 out of 5 average rating, 107 reviews

Premier St Michaels Cottage- In Town Location

Jan 10 – 17

R6,350 ZAR per night
Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 134 reviews

Sunset Breezes - quiet waterfront retreat

Oct 22 – 29

R5,927 ZAR per night
Superhost

Home in Cambridge

4.89 out of 5 average rating, 110 reviews

Dorothy's Chesapeake Delight

Apr 4 – 11

R2,804 ZAR per night
Guest favorite

Home in Oxford

4.97 out of 5 average rating, 183 reviews

The Oxford House

Mar 12 – 19

R5,556 ZAR per night
Superhost

Home in Easton

4.84 out of 5 average rating, 123 reviews

The Farm House at Hunting Creek - Pets $50 a night

Mar 14 – 21

R8,593 ZAR per night
Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 195 reviews

Cape St Claire waterfront getaway

Sep 26 – Oct 3

R2,723 ZAR per night
Superhost

Home in Queenstown

4.81 out of 5 average rating, 143 reviews

Bay Breeze Retreat

Apr 26 – May 3

R17,163 ZAR per night

Other great vacation rentals in Saint Michaels

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 152 reviews

Blackwater Refuge House on The Farm, water access

May 24 – 31

R2,050 ZAR per night
Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 310 reviews

Adorable Waterfront Apartment Weekend Getaway

Jan 14 – 21

R1,665 ZAR per night
Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 202 reviews

Waterfront Getaway - View of bay from your bed

Nov 8 – 15

R5,351 ZAR per night
Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 202 reviews

Eastern Shore Charm on Winchester Creek

Aug 21 – 28

R2,511 ZAR per night
Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

Aug 16 – 23

R2,340 ZAR per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov 29 – Dec 6

R1,593 ZAR per night
Guest favorite

Houseboat in Grasonville

4.99 out of 5 average rating, 113 reviews

Cass-Away A Luxury Houseboat

Feb 2 – 9

R3,299 ZAR per night
Guest favorite

Guest suite in Cambridge

4.95 out of 5 average rating, 265 reviews

Oakley Suite

Nov 17 – 24

R2,802 ZAR per night
Guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 469 reviews

Beach Highway Hobby Farm

Sep 14 – 21

R1,556 ZAR per night
Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Feb 25 – Mar 4

R2,455 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 202 reviews

Calico Cottage Guest House, king bed, free parking

Nov 14 – 21

R1,853 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 102 reviews

Coastal Waterfront 1 Bedroom Cottage

Apr 29 – May 6

R7,183 ZAR per night

Quick stats about vacation 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

R1,894 ZAR before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Saint Michaels?

    Yes! Work meets play with ease at over 20 vacation rentals in Saint Michaels featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Saint Michaels?

    Four-legged friends are welcome in Saint Michaels. Choose from more than 20 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Saint Michaels?

    Experience the best of Saint Michaels with our house rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Saint Michaels have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Saint Michaels. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Saint Michaels have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Saint Michaels. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Saint Michaels have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Saint Michaels. Enjoy a tailored experience with all the comforts you desire.

  • Are there Saint Michaels vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Saint Michaels, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Saint Michaels?

    Saint Michaels has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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