Vacation rentals in Westover

4.89 out of 5 average rating, 283 reviews

A private garden setting is presented, featuring a grassy area surrounded by mature trees and shrubs. A pathway made of stones leads through the garden, while a bench is positioned amidst the greenery, providing a serene spot for relaxation.

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.

4.95 out of 5 average rating, 123 reviews

A vibrant red kettle is positioned on a stove, reflecting light from nearby fixtures. Behind it, a floral arrangement adds color to the countertop, and various kitchen appliances are visible, including a microwave and a sink. The backsplash features green and cream tiles.

Loft in Salisbury

Tree Top Loft

Studio apartment is located on a wooded lot in a quiet neighborhood within 4 miles of Salisbury University & Downtown! Off street parking at entrance patio & a flight of stairs leads up to the apartment, which includes a queen size bed, full kitchen with full size refrigerator, 4 burner electric stove, full size washer and dryer. Bathroom includes shower, toilet and vanity, perfect for a week or weekend stay! We are located near Ocean City, Maryland, Assateague National Seashore.

4.99 out of 5 average rating, 203 reviews

The historic building features prominent columns at its entrance, adorned with vibrant banners displaying the words 'Make Tomorrow Yours.' A neatly landscaped garden with bright green shrubs enhances the building's inviting appearance under a clear blue sky.

Home in Salisbury

Salisbury Cottage

Relax in a quiet part of Salisbury in this cozy, 3 bedroom, 2 full bath home. A farmhouse feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island. One mile from Tidal Health PRMC and a half block away from Salisbury University.

4.96 out of 5 average rating, 287 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, 127 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, 65 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, 210 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.

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.

4.84 out of 5 average rating, 135 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.

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, 145 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, 113 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.

4.96 out of 5 average rating, 134 reviews

A historical marker stands prominently, detailing the significance of Smith Island in Maryland's history. The marker features the state seal and provides information about its founding and early settlements. Background elements include fields and structures, indicative of the island's rural character.

Home in TYLERTON

3 bedroom/2.5 bath Smith Island bungalow with dock

The Quietness of the island and the beautiful scenery around the waters edge. You will hear the birds and the waves and the wind. The island is void of loud noises, mostly nature. The home was built around 1860 and fully restored 2008. its perfectly imperfect!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Westover vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Westover

Home in Deal Island Historic District

4.97 out of 5 average rating, 29 reviews

Rusty Anchor

RachelRating, 5 stars1 week 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.

4.93 out of 5 average rating, 46 reviews

A compact kitchen area features a countertop with a sink and stove, alongside a decorative turquoise bench adorned with a tropical-themed pillow. Natural light filters through a window, enhancing the warmth of the wooden cabinetry and surrounding decor.

Camper/RV in Salisbury

There is no place like GNOME! Camping on a farm!

JoshuaRating, 5 stars2 weeks ago

A super fun, and unique location! We had a great time exploring the local area; restaurants and shopping. And, we all slept so well! Very peaceful surroundings. The wake up call from the peacock was FANTASTIC!

4.98 out of 5 average rating, 103 reviews

A modern kitchen space is showcased with a polished granite countertop and a sleek faucet. The window allows natural light to illuminate the area, while decorative items, including a crab figure, enhance the coastal theme. Clean lines and a subtle colour palette contribute to the overall aesthetic.

Home in Quantico

One of a kind waterfront home with private dock

ZoeyRating, 5 stars2 weeks ago

This was one of my favorite stays so far! The location was quiet and peaceful with beautiful views all around. The dock in the backyard was nice, my dogs loved the fenced in yard and big yard to the side of the house. The house was clean and the bed was super comfortable. I can’t wait to come back! 😊

5 out of 5 average rating, 8 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

JimmyRating, 5 stars1 week ago

We loved our stay at Melanie's place! Waking up to the sound of crashing waves was the highlight of our stay. Melanie's parents were so kind to us and let us use their part of the private beach. They also gave us some delicious Maryland Blue Crab they caught right at the beach. This is very hard to top!

5 out of 5 average rating, 8 reviews

A modern bathroom features three round mirrors above a double sink vanity with brushed metal faucets. The space incorporates navy blue cabinetry and light-colored stone countertops. A separate shower area is visible, with a textured wall and wooden bench, on the right side of the image.

Boat in Kinsale

Spend the Night on the River

AngelaRating, 5 starstoday

What a fun, non traditional location for an overnight. Loved being on the water and close to the activities at The Slips. Annie was great at communication. Can’t wait to stay again.

4.86 out of 5 average rating, 22 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 stars1 week 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!