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Westover Holiday Rentals

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Our top choices for Westover holiday rentals

1. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (58 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is NZ$317
includes taxes & fees
23 Aug - 24 Aug
Cottage near the Bay

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

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (22 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.
The price is NZ$430
includes taxes & fees
19 Aug - 20 Aug
Cozy Barn Loft: Country Views & Central to Beaches

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, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is NZ$417
includes taxes & fees
23 Aug - 24 Aug
Tangier Escape, great place get away from it all on Deal Island, MD.

4. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (615 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is NZ$415
includes taxes & fees
8 Sept - 9 Sept
Key West Cottages

5. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (60 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.
The price is NZ$471
includes taxes & fees
27 Aug - 28 Aug
Deal Island Bay Cottage

6. 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.
The price is NZ$554
includes taxes & fees
17 Aug - 18 Aug
Salisbury Hideaway

7. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (26 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is NZ$429
includes taxes & fees
14 Sept - 15 Sept
Salisbury Riverfront Lofts

8. 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, (23 reviews)
"First time using VRBO and it was more than inexpected"
United States
Robert J.
The price is NZ$324
includes taxes & fees
25 Aug - 26 Aug
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

9. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (308 reviews)
"Experience was amazing! Amenities great! Clean resort, quiet, relaxing…all we hoped for! Will be back!!!!"
United States
Christine
The price is NZ$604
includes taxes & fees
20 Aug - 21 Aug
Blufin Bungalows & Marina

10. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"The cottage was comfortable and met our expectations. We were in Salisbury to visit family and were familiar with the area since we had lived there for many years."
United States
Fred W.
The price is NZ$626
includes taxes & fees
17 Aug - 18 Aug
Salisbury Cottage

11. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (66 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
The price is NZ$757
includes taxes & fees
23 Aug - 24 Aug
The purple door at the bay.

12. Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is NZ$593
includes taxes & fees
19 Aug - 20 Aug
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

13. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is NZ$699
includes taxes & fees
20 Aug - 21 Aug
2 Mi to Downtown: Tranquil Abode in Chincoteague!

14. 6 Mi to Salisbury: Forest-View Sanctuary!

6 Mi to Salisbury: Forest-View Sanctuary!
Parsonsburg
9.8 out of 10, Exceptional, (6 reviews)
"Awesome place "
United States
Rebecca M.
The price is NZ$465
includes taxes & fees
19 Aug - 20 Aug
6 Mi to Salisbury: Forest-View Sanctuary!

15. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is NZ$979
includes taxes & fees
8 Sept - 9 Sept
Bayfront Modern Retreat • Dock, Kayaks, Views

16. Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!
Smith Island
9.6 out of 10, Exceptional, (52 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
The price is NZ$547
includes taxes & fees
7 Sept - 8 Sept
Historic home on Smith Island w/ dock!

17. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (30 reviews)
"Had a great stay! Place was very clean and host was great a communication."
United States
Jen G.
The price is NZ$356
includes taxes & fees
14 Sept - 15 Sept
Assateageue Inn 104 by Seaside Vacations & Sales

18. Entire Private Home • Sleeps 6 • Prime Salisbury Location

Entire Private Home • Sleeps 6 • Prime Salisbury Location
Salisbury
10.0 out of 10, Exceptional, (1 review)
"The stay was great. "
United States
Nathaniel N.
The price is NZ$601
includes taxes & fees
10 Sept - 11 Sept
Entire Private Home • Sleeps 6 • Prime Salisbury Location

19. Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Lauren P.
The price is NZ$326
includes taxes & fees
15 Sept - 16 Sept
Assateague Inn 213 by Seaside Vacations & Sales

20. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (139 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is NZ$769
includes taxes & fees
25 Aug - 26 Aug
Pet-friendly creekside cottage w/ backyard
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

Find out more about Westover

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Westover holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Westover. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Westover. Seeing all the best attractions is bound to make you fall in love with Westover. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Westover short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Westover?

Yes, there are holiday rentals close to the most popular sights in Westover, or you can select a more secluded option if you're looking for a relaxing stay. Westover is known for its golf courses.

What are some of the best holiday rentals that Westover has to offer?

Blufin Bungalows & Marina: This holiday 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 holiday rentals are there in Westover?

Expedia has 6 holiday rentals for your stay in Westover.

What can I see and do in Westover?

Maddox Island and Fishing 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 holiday rental in Westover like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westover. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip.