Saint Michaels vacation rentals

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Top-rated vacation rentals in Saint Michaels

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Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 425 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 17 – 24

$182 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.

Nov 17 – 24

$270 per night

Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 162 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Feb 16 – 23

$108 per night

Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 303 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!

Mar 20 – 27

$110 per night

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 545 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Nov 19 – 24

$125 per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Aug 4 – 11

$489 per night

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Aug 9 – 16

$129 per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 315 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Sep 24 – Oct 1

$77 per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 174 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

Feb 20 – 27

$204 per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 156 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Aug 22 – 29

$93 per night

Guest favorite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 330 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

Oct 21 – 28

$121 per night

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 178 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

Sep 28 – Oct 5

$109 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Saint Michaels vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Saint Michaels

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 116 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Jan 11 – 18

$356 per night

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 141 reviews

Sunset Breezes - quiet waterfront retreat

Nov 29 – Dec 6

$332 per night

Guest favorite

Home in Lusby

5.0 out of 5 average rating, 111 reviews

Historic Rousby Hall, Waterfront, Patuxent River

Jun 25 – Jul 2

$770 per night

Guest favorite

Home in Annapolis

4.99 out of 5 average rating, 198 reviews

Cape St Claire waterfront getaway

Nov 13 – 20

$126 per night

Guest favorite

Home in Kent Narrows

5.0 out of 5 average rating, 277 reviews

Chester Riverfront At Kent Narrows

Oct 19 – 26

$318 per night

Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 225 reviews

River Front, Private Single Family Home

Nov 3 – 10

$416 per night

Superhost

Home in Cambridge

4.89 out of 5 average rating, 111 reviews

Dorothy's Chesapeake Delight

May 13 – 20

$140 per night

Guest favorite

Home in Lusby

4.98 out of 5 average rating, 261 reviews

Cove Point Beach Cabin

Jan 15 – 22

$150 per night

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Other great vacation rentals in Saint Michaels

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Jul 14 – 21

$85 per night

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 311 reviews

Coastal Treetop Retreat w/ Private Beach Access

Jan 2 – 9

$112 per night

Guest favorite

Guest suite in Cambridge

4.96 out of 5 average rating, 267 reviews

Oakley Suite

Sep 9 – 16

$117 per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 207 reviews

Waterfront Getaway - View of bay from your bed

Oct 31 – Nov 7

$248 per night

Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 203 reviews

Eastern Shore Charm on Winchester Creek

Aug 21 – 28

$115 per night

Guest favorite

Houseboat in Grasonville

4.99 out of 5 average rating, 116 reviews

Cass-Away A Luxury Houseboat

Jan 14 – 21

$150 per night

Guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 479 reviews

Beach Highway Hobby Farm

Nov 17 – 24

$72 per night

Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 496 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov 19 – 26

$73 per night

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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
2.8K reviews
Nightly prices starting at
$110 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 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.
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!

Saint Michaels vacation rentals

Top-rated vacation rentals in Saint Michaels

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Saint Michaels vacation rentals

Stay near Saint Michaels's top sights

Other great vacation rentals in Saint Michaels

Home in Shady Side

Home in Cambridge

Home in Lusby

Home in Annapolis

Home in Kent Narrows

Home in Grasonville

Home in Cambridge

Home in Lusby

Other great vacation rentals in Saint Michaels

Guesthouse in Annapolis

Loft in Lusby

Guest suite in Cambridge

Guesthouse in Stevensville

Guesthouse in Grasonville

Houseboat in Grasonville

Apartment in Greenwood

Tiny home in Cambridge

Quick stats about vacation rentals in Saint Michaels

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

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

Are there pet-friendly vacation rentals in Saint Michaels?

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

Do house rentals in Saint Michaels have wifi?

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

Do house rentals in Saint Michaels have a bbq area?

Are there family-friendly house rentals in Saint Michaels?

Are there Saint Michaels vacation rentals on Airbnb with pools?

Destinations to explore