Vacation rentals in Janes Island

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Top-rated vacation rentals in Janes Island

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

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Top guest favorite
Home in Smith Island
4.96 out of 5 average rating, 23 reviews

Come enjoy Summer on Smith Island at the HH Ranch

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

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Top guest favorite
A rustic cabin is surrounded by tall pine trees, featuring a spacious deck with multiple seating areas. An American flag is displayed, while a grill is positioned nearby. Large windows allow natural light into the interior, creating a welcoming exterior view.
Cabin in Onancock
4.96 out of 5 average rating, 71 reviews

Awesome private off grid Creek front Cabin.

Feel refreshed when you stay in this rustic gem. You will have 100 acres of private land, family owned since 1818. Creek access for fishing, canoeing, etc. Come and unplug in peace and quiet away from the hustle and bustle. Access to the Cheasapeake Bay or the Atlantic is a short drive away. Enjoy the daily sites of deer, turkey, waterfowl, eagles and osprey among dozens of other wildlife. Cabin is 1 mile off the road down a private dirt road. This is a rare experience to sample off grid living.

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Top guest favorite
A large wooden deck features several adirondack chairs positioned to face expansive views of the marshland and water. A clear blue sky complements the serene landscape, with gentle clouds casting soft shadows over the scene.
Home in Parksley
5 out of 5 average rating, 23 reviews

Serene Waterfront Metompkin Retreat - Entire Home

Discover serenity at the ultimate retreat on Virginia's Eastern Shore at our waterfront oasis. Indulge in sweeping panoramic views of the tranquil waters that stretch as far as the eye can see. Nature enthusiasts will delight in the abundance of birdlife, making it a true birdwatcher's paradise. Whether sipping coffee on the private deck at sunrise or enjoying a glass of wine while watching the sunset paint the sky, every moment here is a picture-perfect postcard. A truly unforgettable getaway.

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Top guest favorite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby
4.98 out of 5 average rating, 112 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

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Top guest favorite
A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.
Home in Lusby
4.95 out of 5 average rating, 140 reviews

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

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Top guest favorite
The exterior of a modern, single-story house features a light blue façade with contrasting dark shingles. A wooden staircase leads to the front door, while a small deck is visible to the left. A paved walkway runs along the well-maintained lawn.
Home in Crisfield
4.99 out of 5 average rating, 103 reviews

Marshall’s Retreat Chesapeake small town getaway

Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes from our towns new bike trail, boat & Kayak launch, park play ground,Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise (within walking distance), beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs.

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Top guest favorite
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, 164 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!

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Guest favorite
Cottage in Westover
5 out of 5 average rating, 10 reviews

Eastern Shore Private Sandy Beach & Crabbing dock!

Marvel at the breathtaking 360 views from every window throughout the house! The wraparound decks and private balconies are the perfect locations to take in the amazing expansive waterfront views in every direction! Stroll the 150’ boardwalk and enjoy the water views leading to a 200’ pier and 20’ x 20’ dock with boat slip for the avid boater. You will see nature all around you. Fish, crab or just relax off the dock while enjoying the spectacular views and most amazing sunsets!a s n m

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Guest favorite
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
4.78 out of 5 average rating, 278 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.

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Top guest favorite
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
4.97 out of 5 average rating, 199 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.

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Top guest favorite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover
4.99 out of 5 average rating, 263 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

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Guest favorite
A spacious yard features a hammock suspended between two trees, overlooking the bay. Colorful Adirondack chairs are positioned nearby, creating an inviting spot for relaxation. The calm water stretches into the distance under a clear sky, providing a serene atmosphere.
Cottage in Reedville
4.88 out of 5 average rating, 261 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

180 degree million dollar views in the quaint town of Reedville, VA. Away from all the noise, you won't want to leave our cottage once you get here. Upstairs bedroom has a private balcony with breathtaking views. Bay views from almost every window in the house. Perfect getaway for couples or the whole family. 60 inch Smart TV! Come build some memories!

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Popular amenities for Janes Island vacation rentals