We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

Home in Solomons

4.96 out of 5 average rating, 23 reviews

Solomons Yellow House - Waterfront

This is a beautiful completely renovated light filled historic waterfront 3 bedroom house in the Avondale section of Solomons, MD. Solomons is a historic fishing village on the Western Shore of the Chesapeake Bay and is bounded by the Patuxent River to the South. Baltimore and DC are less than an hour away. The property slopes gently down to a private & protected cove of the Chesapeake Bay. There is a crab shack and dock where sunsets can be viewed and cocktails appreciated.

Home in Mechanicsville

4.92 out of 5 average rating, 12 reviews

Modern luxury waterfront - Fall retreat

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Home in Deale

4.96 out of 5 average rating, 25 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Cottage in Pasadena

4.82 out of 5 average rating, 17 reviews

Sunset Lagoon Home

Have fun with the whole family at this stylish place! Our cozy cottage sits at the edge of a beautiful creek. Peaceful and tranquil, yet close to shops and restaurants, this waterfront property is perfect for serene getaways and family gatherings! Everyone will enjoy a unique and private space to relax. From peaceful mornings lounging on the balconies, to afternoons filled with fishing and kayaking, to magical sunsets on the 110-foot pier, this setting will quickly become a family favorite!

Home in Cambridge

4.98 out of 5 average rating, 121 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Come relax at our casual, pristine waterfront home. We offer 4 bedrooms w/7 beds for 10 guests. We are nestled in a small neighborhood on the beautiful Choptank River. We provide bikes, kayaks, paddleboards & yard games. Just want to relax? Enjoy hanging in the hammock or kick back on the waterfront w/a private pier. Try fishing off the pier or simply chill on the back deck or patio. At night hang out by the firepit. Explore downtown Cambridge - it's a short walk/bike ride to town.

Cottage in Colonial Beach

5 out of 5 average rating, 26 reviews

Resting Beach Face Charming River-View Cottage

Do you need a break from the kids, or your spouse? A weekend away with your girlfriends? We've got the perfect place for you! Our charming cottage is on a quiet street with views of the Potomac River. With 2 bedrooms and 1.5 baths, we can accommodate 2-4 adults comfortably. Sleep late. Take a stroll along the water. Rent a golf cart. Cruise around town. Hit the beach. Visit a vineyard. Grab some dinner. Listen to live music. Chill on the porch swing. Go home relaxed and refreshed!

Cottage in Heathsville

4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

Cottage in Pasadena

4.88 out of 5 average rating, 121 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Cottage in Colonial Beach

4.93 out of 5 average rating, 168 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Home in Lusby

4.87 out of 5 average rating, 55 reviews

Beachfront Oasis with Amazing Views

Perfect getaway home to relax and enjoy peaceful beach views. This beachfront home is perfect for a romantic weekend getaway or a family vacation. Enjoy long walks on the beach, conversations at the fire pit in the evening, kayaking or hunting for fossil sharks teeth. The perfect escape from DC, the home is just over an hour from the city and located in the quiet, private beach community.

Rental unit in Betterton

5 out of 5 average rating, 15 reviews

Bayside Bungalow

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

Home in Saint Michaels

4.91 out of 5 average rating, 168 reviews

Dr. Miller house. Best location-in the heart town

This renovated house is conveniently located in the heart of one of the cutest towns in the USA. Walk to everything! There are fantastic shops, restaurants, a winery, a brewery, coffee shops, museums and only 3 blocks from the water. Park your car at the house and never have to use it!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Saint Michaels vacation rentals

Laptop-friendly workspace

Stay near Saint Michaels's top sights

Chesapeake Bay Maritime Museum39 locals recommend

Ava's Pizzeria & Wine Bar - St. Michaels20 locals recommend

Foxy's Harbor Grille17 locals recommend

Patriot Cruises12 locals recommend

The Crab Claw11 locals recommend

Gina's Cafe11 locals recommend

Saint Michaels home rentals

Home in Northwest Washington

5 out of 5 average rating, 8 reviews

New Cozy Home In NW DC Sleeps 12

Home in Arlington

4.78 out of 5 average rating, 264 reviews

Newly renovated; mins to DC, airport, food, metro

Home in Northeast Washington

4.86 out of 5 average rating, 50 reviews

Super Host Renovated Home. Sleeps 6. EZ parking.

Home in Montross

4.94 out of 5 average rating, 189 reviews

The Glebe

Home in Salisbury

4.98 out of 5 average rating, 195 reviews

Beautiful Renovated Home, Perfect Getaway!

Home in Cambridge

4.95 out of 5 average rating, 223 reviews

Great Historic Cambridge Home With Parking!

Home in Northwest Washington

4.87 out of 5 average rating, 202 reviews

DC Row home w/private apt by Rock Creek Park

Home in Pentagon City

4.93 out of 5 average rating, 153 reviews

Thanksgiving | LA Inspired Glasshouse 4min DC

Other great vacation rentals in Saint Michaels

Home in Fruitland

4.97 out of 5 average rating, 127 reviews

Amazingly convenient yet secluded.

Home in Edgewater

4.92 out of 5 average rating, 138 reviews

House in Edgewater Maryland

Rental unit in Canton

5 out of 5 average rating, 25 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

Cottage in Deale

4.82 out of 5 average rating, 176 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Home in Montross

4.84 out of 5 average rating, 132 reviews

Potomac Waterfront Home and Estate

Home in Montross

4.89 out of 5 average rating, 224 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Cabin in Lusby

4.84 out of 5 average rating, 159 reviews

2-bedroom lake-house with a magnificent view

Home in Colonial Beach

4.94 out of 5 average rating, 64 reviews

The Heaven at Colonial Beach

Quick stats about vacation rentals in Saint Michaels

Total rentals
40 properties
Nightly prices starting at
G$29,242 GYD before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

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.
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!
How much does it cost to stay in apartment rentals in Saint Michaels?
Experience the best of Saint Michaels with our apartment rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Saint Michaels have wifi?
Absolutely! We offer over 10 apartment 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.

Destinations to explore