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Westover Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Westover vacation rentals

Interior

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
$176 nightly
The price is $187
Sep 21 - Sep 22
Total with taxes and fees
Cottage near the Bay
Apartment D: Riverfront Grand | 2 bedrooms, iron/ironing board (on request), WiFi (free)

2. 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
$226 nightly
The price is $242
Oct 19 - Oct 20
Total with taxes and fees
Salisbury Riverfront Lofts
Beach

3. 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 25 - Sep 26
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
Cottage (2 Bedrooms) | Interior

4. Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
Pet-friendly Smith Island Cottage w/ Golf Cart!
Exterior

5. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (327 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
$179 nightly
The price is $201
Sep 23 - Sep 24
Total with taxes and fees
Blufin Bungalows & Marina
Exterior

6. Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell
10.0 out of 10, Exceptional, (23 reviews)
"The Castaway house was a wonderful spot for our family of 4. The house was so comfortable and it was fantastic to have access to the golf cart to tour the island!! The island was very welcoming. One highlight was a boat tour with Capt. Mark Kitching (410)603-1227. He took us through the marshes and outer islands, pointing out lots of birds (we saw Pelicans!!). Bring your own food if you want to cook- restaurants close early and groceries are limited. Cash or check for the boat over. It...
United States
Laura J.
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Coffee/tea maker, fridge, microwave, oven

7. 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 20 - Sep 21
Total with taxes and fees
Cozy Barn Loft: Country Views & Central to Beaches
Coffee/tea maker, fridge, microwave, oven

8. 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.
$245 nightly
The price is $259
Oct 4 - Oct 5
Total with taxes and fees
Deal Island Bay Cottage
Coffee/tea maker, fridge, microwave, oven

9. 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.
$176 nightly
The price is $186
Sep 21 - Sep 22
Total with taxes and fees
Retro Hipster: Close to downtown, dining and fun
Smart TV, offices

10. 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.
$433 nightly
The price is $477
Sep 22 - Sep 23
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
Interior

11. 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
$367 nightly
The price is $412
Sep 26 - Sep 27
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Palm Cottage | 1 bedroom, premium bedding, laptop workspace, soundproofing

12. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (641 reviews)
"This was the perfect relaxing get away! Clean and quiet! Already booked for next spring 2027!"
United States
LaTonya
$224 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
Key West Cottages
Exterior

13. 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.
$328 nightly
The price is $348
Sep 28 - Sep 29
Total with taxes and fees
Salisbury Hideaway
Smart TV, offices

14. 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.
$329 nightly
The price is $349
Oct 6 - Oct 7
Total with taxes and fees
Salisbury Cottage
TV

15. Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.8 out of 10, Exceptional, (8 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
$184 nightly
The price is $192
Sep 20 - Sep 21
Total with taxes and fees
Assateague Inn 106 by Seaside Vacations & Sales
TV, DVD player

16. 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
Sep 21 - Sep 22
Total with taxes and fees
Assateageue Inn 104 by Seaside Vacations & Sales
Interior

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 21 - Sep 22
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
Beach nearby

18. 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.
$356 nightly
The price is $400
Sep 25 - Sep 26
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
2 bedrooms, desk, iron/ironing board, travel crib

19. 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
Marina

20. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$326 nightly
The price is $360
Sep 20 - Sep 21
Total with taxes and fees
Come out and enjoy Autumn at the HH Ranch on Smith Island.
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

Waterside Inn

Waterside Inn

10/10 Excellent
"The view from the windows was magnificent. To sit on the balcony and to see the beautiful sunset was incredible. The pool was clean and the last day was really warm probably because was heated. To be at the pool and see the bay was very calming and relaxing. Definitely will come back to this place again"
Margarita 2-night trip
Posted 22 hours ago
Waterside Inn

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 $201 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.