Vacation rentals in Saint Michaels

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Top-rated vacation rentals in Saint Michaels

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Guest favourite

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.

Guest favourite

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.

Guest favourite

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.

Superhost

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!

Guest favourite

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.

Guest favourite

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!

Guest favourite

Villa in Easton

4.95 out of 5 average rating, 44 reviews

St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

FALL BONUS. EARLY CHECKIN! Breathtaking views, private pool with baja deck, pier with boat slip, kayaks for 10, 4 bikes, and gas firepit by the water! Great for two families/multi-generations. Two primary bedroom suites and great water views from every room. Listing 347588 on vacation rental by owners. Extensive feedback on that site! 7 days during summer. PETS are $45 per pet per day Must get approval! Pool can be heated at a surcharge. Talbot County license: ST 809 GOL

Superhost

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!

Guest favourite

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.

Guest favourite

Camper/RV in Abell

5 out of 5 average rating, 75 reviews

Waterfront at the Pines of Canoe Neck

Welcome to "The Pines at Canoe Neck" a private waterfront experience with the farm feel. Enjoy the 75 foot dock with fishing, crabbing, canoeing, kayaking and much more on the quiet inlet. Private docking available for personal boats. Guests have the option of visiting the cute critters living on the property as well as an abundant garden full of you pick seasonal veggies, all you can pick and eat for the stay.

Guest favourite

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.

Guest favourite

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!