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Holiday houses in Smith Island

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Top-rated holiday rentals in Smith Island

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Guest favourite
A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.
Cottage in Hacksneck
4.95 out of 5 average rating, 143 reviews

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Top Guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 248 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Guest favourite
Cottage in Reedville
4.91 out of 5 average rating, 219 reviews

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

Guest favourite
A screened-in porch features a light-colored door and multiple large windows, providing an unobstructed view of the outdoors. The adjacent landscaping includes colorful flower beds with a mix of vibrant marigolds and greenery, complemented by a wooden staircase leading up to the entrance.
Cottage in Reedville
4.94 out of 5 average rating, 153 reviews

Bull Neck Cottage

The cottage is located near "downtown" Reedville and provides a clean, comfortable and economical getaway. Come and enjoy water related activities and beautiful sights of Virginia's Northern Neck and the Chesapeake Bay. Tour the Watermen's Museum; cruise across the Chesapeake Bay to Tangier Island; walk, bike or kayak around Reedville, take a fishing charter or launch your boat nearby; enjoy great waterfront seafood restaurants; or just relax with a book.

Top Guest favourite
A charming farmhouse is illuminated by soft string lights, creating a serene ambiance at dusk. A wooden fence lines the yard, and stairs lead to an entrance on the upper level. Light fog lingers near the ground, enhancing the peaceful atmosphere.
Farm stay in Heathsville
4.99 out of 5 average rating, 108 reviews

Fleets Cove Farm *PETS STAY FREE*

Welcome to Fleets Cove Farm y'all! Looking for a peaceful and secluded place to stay? We have the place for you! With expansive fields surrounded by tall hardwood trees, it's hard not to love the light breeze and quiet. At night, sitting around the fire pit and looking at the stars is a must. The mini donkeys and cows are always looking for new friends. We also have seasonal animals like pigs, chickens, and ducks at different times of the year.

Guest favourite
The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.
Guest suite in Crisfield
4.77 out of 5 average rating, 257 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Top Guest favourite
A view from the entrance captures the cozy interior of the houseboat. The kitchen area features a wooden countertop and a black sink. Light wood and black hexagonal flooring complement the bright space, while large windows provide glimpses of the water outside.
Houseboat in Solomons
4.98 out of 5 average rating, 164 reviews

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

Guest favourite
A rustic cabin is surrounded by lush trees, with a welcoming porch showcasing seating. The exterior features wooden panels and large windows, allowing natural light to fill the interior while maintaining privacy. A gravel path leads to the entrance, enhancing the natural landscape.
Guesthouse in Saluda
4.94 out of 5 average rating, 571 reviews

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax.

Top Guest favourite
The exterior of Waterman’s Hideaway features a welcoming entrance with a wooden fence and pathway leading to the house. Lush green grass surrounds the property, complemented by a shaded tree. The coastal-inspired structure showcases a green roof and charming architectural details.
Home in Tangier
4.98 out of 5 average rating, 179 reviews

Watermans Hideaway, Tangier Island, Chesapeake Bay

The Waterman’s Hideaway is a two story, coastal inspired home located on main street at the center of town and a short walk from Tangier’s restaurants, gift shops and tour boat docks. Guests can enjoy the deck overlooking the spacious backyard or lounge under the shade tree at the front of the property where they can interact with the locals passing bye as they go about their daily routines.

Top Guest favourite
A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.
Apartment in Irvington
5 out of 5 average rating, 111 reviews

Pelican Place, Cozy Retreat | Pool | Walk to Tides

Unwind at this stylish apartment with view of Carters Creek and walking distance to the cutest little town and the iconic Tides Inn Resort. Take a refreshing dip in the pool, enjoy the charming outdoor shower, and star gaze under a blanket from the rooftop deck. Several outdoor spaces and large yard with whimsical touches. The perfect hideaway close to all the Northern Neck has to offer.

Top Guest favourite
The exterior of the cottage is shown, featuring a welcoming entryway with stairs and a blue door. Two blue adirondack chairs are positioned on the well-maintained lawn, with a glimpse of the waterfront visible through large windows. Surrounding greenery enhances the outdoor setting.
Cottage in Smith Island
4.97 out of 5 average rating, 247 reviews

Levering Creek Cottage with private dock

Levering Creek Cottage is a waterfront property with a deep water dock that you can see from the back door. We are located on Levering Creek where you can sit on the dock watching watermen arrive with their daily catch, see nesting bald eagles, watch beautiful sunrise, fish and crab. We are also just steps away from most everything including the ferry.

Top Guest favourite
A one-story white house is surrounded by a green lawn and is enclosed by a fence. The home features a peaked roof and small front porch, with large windows allowing natural light. A decorative sign is positioned in front, marking the property.
Home in Tangier
5 out of 5 average rating, 138 reviews

Island Oasis, Tangier Island, Virginia

Island Oasis is a one story, waterfront, newly renovated home situated in the heart of town. The tour boat docks are directly behind property with a gift shop on site. Restaurant, ice cream/sandwich deck, grocery store, church, museum , etc are all within walking distance. Guests will have full access to home and a nice deck overlooking harbor.

Popular amenities for Smith Island holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Somerset County
  5. Smith Island