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, 26 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, 13 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.

Guest favourite

Home in Deale

4.96 out of 5 average rating, 28 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.

Guest favourite

Home in Centreville

5 out of 5 average rating, 22 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.

Superhost

Cottage in Saint Michaels

4.84 out of 5 average rating, 31 reviews

Cottage #8 Herons Nest Lg 2 rooms Under Main House

OPEN March 25th to Nov 1st. every year. Herons Nest no 8 is located under main house, consist of full Kitchen, dining table, 1 queen size bed in separate bedroom, Living room Full size Futon open to a bed, 2 large sleeper recliners. Please call Jaimie upon arrival. No pets allowed! We no longer provide bed linens, Coffee, sugar or creams. or Towels. Boats are rentals! room tax 4% due on arrival , 6% Abb collects please Bring waters . Boat info below. If need air mattress can bring.

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!

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 Easton

5 out of 5 average rating, 101 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

Guest favourite

Home in Cambridge

4.98 out of 5 average rating, 122 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!

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

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.

Guest favourite

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.