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Saint Michaels vacation rentals

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Top-rated vacation rentals in Saint Michaels

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

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Home in Solomons

4.96 out of 5 average rating, 24 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 retreat, 1 hr to DC

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, 26 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.

Home in Centreville

5 out of 5 average rating, 21 reviews

Water Oasis on the Eastern Shore

With incredible views of the Corsica River from almost every room and set on 6 acres amidst idyllic farms, your home away from home calls. A 5-bedroom, 6.5-bath waterfront oasis, Middle Fox Cove is the key to unlocking a memorable getaway you will never want to leave behind. This 5000 square foot home is a tranquil masterpiece that makes room for relaxing and recreating. Bring the entire family or just a quiet retreat for two - make this the memorable experience you’ve been looking for.

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 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 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 to magical sunsets on the 110-foot pier, this setting will quickly become a family favorite!

Cottage in Easton

5 out of 5 average rating, 100 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Home in Cambridge

4.98 out of 5 average rating, 121 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

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

4.88 out of 5 average rating, 56 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.

Apartment 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

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

House rentals in Saint Michaels

Home in Arlington

4.78 out of 5 average rating, 270 reviews

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

Home in Capitol Hill

4.95 out of 5 average rating, 176 reviews

Beautiful Capitol Hill Row House

Home in Northwest Washington

4.85 out of 5 average rating, 167 reviews

Chez ChEllers

Home in Salisbury

4.98 out of 5 average rating, 195 reviews

Beautiful Renovated Home, Perfect Getaway!

Home in Saint Michaels

4.83 out of 5 average rating, 77 reviews

Harrison House - in Town and on St Michaels Harbor

Home in Rock Hall

4.84 out of 5 average rating, 127 reviews

Pirates Perch

Home in Catonsville

4.74 out of 5 average rating, 146 reviews

Cozy Catonsville Bungalow

Home in Rock Hall

5 out of 5 average rating, 82 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

Other great vacation rentals in Saint Michaels

Home in Fruitland

4.97 out of 5 average rating, 128 reviews

Amazingly convenient yet secluded.

Home in Edgewater

4.91 out of 5 average rating, 139 reviews

House in Edgewater Maryland

Apartment in Canton

5 out of 5 average rating, 26 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

Home in Montross

4.84 out of 5 average rating, 132 reviews

Potomac Waterfront Home and Estate

Cottage in Colonial Beach

4.85 out of 5 average rating, 82 reviews

Bungalow Private Beach & Dock Colonial Beach Water

Home in Montross

4.89 out of 5 average rating, 225 reviews

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

Cabin in Lusby

4.84 out of 5 average rating, 160 reviews

2-bedroom lake-house with a magnificent view

Home in Colonial Beach

4.94 out of 5 average rating, 65 reviews

The Heaven at Colonial Beach

Quick stats about vacation rentals in Saint Michaels

Total rentals
40 properties
Nightly prices starting at
G$29,258 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.
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!

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