Vacation rentals in Westover

4.89 out of 5 average rating, 284 reviews

A tranquil backyard is surrounded by lush greenery, featuring a variety of trees and shrubs. A stone path leads through the garden, inviting peaceful walks. A small seating area can be seen under the shade of a large tree, enhancing the inviting outdoor space.

Tiny home in Snow Hill

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

4.96 out of 5 average rating, 277 reviews

A wide-angle view captures the beach and ocean, with soft waves lapping at the shore. The surrounding buildings are visible, including the condominium structure featuring floor-to-ceiling windows. A beachfront pool and tennis courts occupy the area below, while sunbathers and umbrellas dot the sandy beach.

Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

4.96 out of 5 average rating, 288 reviews

Home in Crisfield

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

4.87 out of 5 average rating, 131 reviews

A charming outdoor area is showcased along a wooden walkway beside the water. Colorful banners and umbrellas adorn the pavilion, while wooden chairs invite relaxation. The grassy space features tiki torches, and boats can be seen docked in the distance under a bright blue sky.

Houseboat in Snow Hill

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.88 out of 5 average rating, 66 reviews

A serene outdoor area is highlighted by a circular stone firepit surrounded by grassy terrain. Nearby, a calm pond reflects the surrounding trees, while wooden picnic tables provide seating for relaxation amidst nature. Lush greenery extends into the distance, enhancing the tranquil setting.

Guest suite in Westover

The Hideaway Suite

Welcome to our humble farmhouse guest suite, your own little slice of tranquility nestled amongst the fields and forests. Tucked away from the hustle and bustle, our home is your perfect getaway, providing peace and quiet while still being conveniently close to Route 13. Once you step inside to the comfort of your suite on the second floor, you're in for a treat with beautiful views and idyllic sunsets. We look forward to hosting you in our lovely farmhouse.

4.75 out of 5 average rating, 212 reviews

The image displays a serene sunset over a body of water, with the sun positioned low on the horizon. Silhouettes of trees and vegetation can be seen along the far shore, contrasting against the warm hues of orange and pink in the evening sky.

Guest suite in Crisfield

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.

5 out of 5 average rating, 103 reviews

A rustic wooden table features a plate of oysters and a bottle of red wine, accompanied by a glass filled with wine. A fire pit emits a warm glow nearby, with the scenic view of a creek and trees in the background.

Loft in Hebron

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

4.99 out of 5 average rating, 227 reviews

A wooden boardwalk extends toward a sandy beach, flanked by tall grasses and wetlands. The peaceful water is visible in the distance under a clear blue sky, with a few clouds adding texture to the scene.

Cottage in Westover

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. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

4.85 out of 5 average rating, 136 reviews

A fire pit is surrounded by four red Adirondack chairs, situated on a gravel surface. Lush green trees form a natural backdrop, enhancing the outdoor space's connection to nature. Two torches are positioned nearby, providing ambient lighting for gatherings.

Tiny home in Salisbury

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

4.98 out of 5 average rating, 281 reviews

A wooden gate opens to a gravel path, leading toward a charming tiny house surrounded by greenery. A colorful sunset casts warm hues over the landscape, while a decorative pergola adorned with climbing plants frames the scene.

Tiny home in Selbyville

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

Guesthouse in Pocomoke City

A gravel driveway meanders through a tree-lined path, bordered by lush green grass. The sunlight filters through the foliage, creating dappled shadows along the way, leading towards an open area.

4.95 out of 5 average rating, 146 reviews

2 Bedroom Apartment

Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.

Guest suite in Deal Island Historic District

A spacious wrap-around deck features a wooden picnic table and a charcoal grill, enhancing outdoor dining options. A lounge chair is positioned nearby, creating an inviting spot for relaxation. The deck's wooden flooring extends along the side of the house, with a view of the surrounding greenery.

4.9 out of 5 average rating, 114 reviews

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.

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Popular amenities for Westover vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

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Other great vacation rentals in Westover

Two chairs are positioned on sandy ground, facing a tranquil bay at sunset. Fishing poles stand upright in the sand beside the chairs, while soft waves reflect shades of orange and pink from the sky. A grassy area frames the scene, enhancing the peaceful atmosphere.

Cottage in Deal Island

4.64 out of 5 average rating, 236 reviews

Deal Island Bay Cottage - Maryland

AshRating, 5 stars1 week ago

Great location. Very rural, quiet neighborhood, very responsive host.

Home in Deal Island Historic District

4.97 out of 5 average rating, 29 reviews

Rusty Anchor

RachelRating, 5 stars2 weeks ago

Rustic and charming, the Rusty Anchor was exactly what we hoped for. The screened porch was a favorite hang out spot. The kitchen sink was absolutely adorable. And the host had tons of family friendly amenities available like a baby bath, beach toys, coloring books, and board games. It looks just like the pictures. Her recommendations for the Washington Inn (now Sugar Water), the local beach, and the produce stand were all fantastic. We didn’t want to leave. If you are looking for a low-key, relaxing get-away, this is the perfect place.

5 out of 5 average rating, 11 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

KylieRating, 5 stars2 days ago

Can’t beat the views. It’s a quick drive into town. There is a great take out seafood restaurant!

4.85 out of 5 average rating, 27 reviews

A sandy beach path is bordered by large stones and water, leading towards the horizon. A dog walks along the shore, with clear blue skies and distant structures visible across the bay.

Home in Princess Anne

Ye Ole Pirate House

BangiRating, 5 stars1 month ago

Our family enjoyed Lisa’s place. She wa very responsive when I had a few questions. The place was very clean, tidy and had everything we needed. My girls played a few board games that were available. I would highly recommend Lisa’s place.

4.87 out of 5 average rating, 23 reviews

A wicker loveseat is displayed on a porch, featuring a striped cushion and two decorative pillows with a floral design. A small round table accompanies the seating, with brick flooring seen beneath. Light is visible through a nearby door leading indoors.

Home in Crisfield

Cozy Crisfield Cottage

LenaRating, 5 stars2 weeks ago

Jackie’s place was perfect- so much space, impeccably clean, stoked with everything we needed, and close to everything we needed! Jackie was so quick to respond to all messages! If we’re ever back in Crisfield, hope to stay here again!

A door opens to reveal a wooden balcony overlooking a serene marsh scene. Sunlight glimmers on the water's surface, with lush green grasses lining the shore. A fishing pole leans against the railing, inviting outdoor activities in this tranquil setting.

Home in Westover

5 out of 5 average rating, 4 reviews

The Salt Marsh Shanty

ScottRating, 5 stars1 week ago

A very comfortable home in a gorgeous setting. The marsh out back is like a small private nature preserve. I spent lots of time watching the bird life and the changing light, as well as the easy kayaking at the doorstep. No noise save for birdsong, and I saw hummingbirds, bald eagles, and lots in between. The house is new and very clean with a well-stocked kitchen and room to unwind. The hosts are thoughtful and provide equipment/supplies to enjoy the water and related activities.

4.84 out of 5 average rating, 37 reviews

A screened-in porch offers a relaxed seating area with a cushioned sofa and two lounge chairs. Natural light fills the space through large windows, providing views of the surrounding greenery. A small dining table for four sits in one corner, enhancing the inviting atmosphere.

Cottage in Westover

Dog-Friendly Westover Cottage w/ River Access!

KelseyRating, 5 stars2 weeks ago

We really enjoyed our stay here! The cabin is right on the water and there are kayaks on site that you can use. The cabin was very clean and the inside was nicely decorated. The kitchen was also well stocked with silverware and cooking supplies which was nice since there are not many restaurants in the area. The only down side were the mosquitos and flies but they do provide bug spray for this. We would definitely stay here again!!