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Westover Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Westover vacation rentals

A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

1. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (62 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
$169 nightly
The price is $179
Sep 27 - Sep 28
Total with taxes and fees
Cottage near the Bay
A sandy beach with footprints, a pier in the distance, and a clear sky.

2. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$232 nightly
The price is $246
Sep 30 - Oct 1
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
A room with a large bed, multiple windows, and a ceiling fan.

3. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
$228 nightly
The price is $245
Oct 23 - Oct 24
Total with taxes and fees
Salisbury Riverfront Lofts
A kitchen with a farmhouse sign, a clock, and a refrigerator.

4. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
$242 nightly
The price is $271
Sep 24 - Sep 25
Total with taxes and fees
Cozy Barn Loft: Country Views & Central to Beaches

5. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (328 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
$175 nightly
The price is $196
Oct 13 - Oct 14
Total with taxes and fees
Blufin Bungalows & Marina
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

6. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
$304 nightly
The price is $341
Sep 30 - Oct 1
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

7. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 reviews)
"We were there for our granddaughter's wrestling tournament in Salisbury. House was excellent, quiet and clean. Beautiful home. Thank you."
United States
Christopher M.
$246 nightly
The price is $261
Sep 24 - Sep 25
Total with taxes and fees
Deal Island Bay Cottage
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

8. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
$350 nightly
The price is $371
Oct 19 - Oct 20
Total with taxes and fees
Salisbury Cottage
A single-story house with a front porch, a door, and a mailbox.

9. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
$301 nightly
The price is $319
Sep 27 - Sep 28
Total with taxes and fees
Salisbury Hideaway
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

10. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
$170 nightly
The price is $180
Sep 28 - Sep 29
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A waterfront house with a balcony, dock, and a view of the water.

11. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (645 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
$224 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
Key West Cottages
A sunroom with wicker furniture, large windows, and a view of the water.

12. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 reviews)
"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."
United States
Francis
$388 nightly
The price is $427
Oct 1 - Oct 2
Total with taxes and fees
The purple door at the bay.
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

13. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"Overall nice stay!"
United States
Becky S.
$452 nightly
The price is $498
Sep 27 - Sep 28
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
A sandy beach with footprints and a person walking.

14. Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
$368 nightly
The price is $413
Sep 24 - Sep 25
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A two-story building with a central entrance and a wooden walkway leading to it.

15. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"Beautiful place. I’ve stayed at Assateague Inn on several occasions over the years but this was my first time in 203 and by far the nicest one I’ve stayed in. Newly renovated and tastefully d"
United States
Annette H.
$195 nightly
The price is $204
Sep 24 - Sep 25
Total with taxes and fees
Assateague Inn 203 by Seaside Vacations & Sales
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

16. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
9.8 out of 10, Exceptional, (9 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A covered porch with wicker chairs and a view of the outdoors.

17. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
$312 nightly
The price is $339
Sep 24 - Sep 25
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

18. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (20 reviews)
"Great alternative to a hotel!"
United States
Courtney L.
$168 nightly
The price is $177
Sep 27 - Sep 28
Total with taxes and fees
Retro Hipster: Close to downtown, dining and fun
A cozy living room with a sofa, a coffee table, and a TV mounted on the wall.

19. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (6 reviews)
"The host was very responsive and brought toys over for our children to help occupy them while we were there. The host is also connected to the Daisey's Island Cruises and gave us a discounted price to take in the cruise while we were on the island. That was very enjoyable and helped us learn more about the island and the annual pony round-up. It suited our family of 5 well."
United States
Cleason H.
$269 nightly
The price is $302
Sep 30 - Oct 1
Total with taxes and fees
Cozy 2-bedroom house in Chincoteague
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

20. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
$184 nightly
The price is $192
Oct 5 - Oct 6
Total with taxes and fees
Assateageue Inn 104 by Seaside Vacations & Sales
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westover Hotel Reviews

Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

10/10 Excellent
"Staff was very helpful. The grounds were very clean. Breakfast was excellent. Room was nice and clean. Loved the view from balcony overlooking the bay. Would definitely recommend this place."
John 2-night trip
Posted 9 hours ago
Comfort Suites Chincoteague Island Bayfront Resort

Find out more about Westover

Everything you need to know about Westover vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westover vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westover vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westover vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westover. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Westover in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $196 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westover rentals

At Expedia, we put the best Westover vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Westover rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westover vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westover. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Westover?

Yes, we offer vacation rentals close to top sights in Westover, or you can go with a more secluded option if you're looking for relaxation. Westover is known for its golf courses.

What's the top vacation rental that Westover has to offer?

Blufin Bungalows & Marina: This vacation home rental outside of Westover is on the beach and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

How many vacation rentals are there in Westover?

Expedia has 5 vacation rentals for your stay in Westover.

What can I see and do in Westover?

Upper Hill Park and Maddox Island are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Great Hope Golf Course and Coventry Parish Ruins.

What’s a vacation rental in Westover like?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Westover. Vacation rentals offer extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.