Westover Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Westover vacation rentals

Exterior
Key West Cottages

Cottage in Downtown Chincoteague

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (494)
"What an absolute wonderful place. Staff were so friendly and the cottages were amazing very clean. We would definitely stay here again."
United States
julie
Key West Cottages
House (3 Bedrooms) | Outdoor dining
6 Mi to Salisbury: Forest-view Sanctuary!

Cottage in Parsonsburg

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
The price is ￥14,349
￥40,112 total
includes taxes & fees
Jan 1 - Jan 2, 2026
6 Mi to Salisbury: Forest-view Sanctuary!
Apartment D: Riverfront Grand | In-room dining
Salisbury Riverfront Lofts

Apartment in Salisbury

Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is ￥11,875
￥40,532 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Salisbury Riverfront Lofts
Dining
Cottage near the Bay

Vacation Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52)
"Great little place "
United States
Eric R.
The price is ￥12,634
￥29,264 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cottage near the Bay
Fridge, microwave, oven, stovetop
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Vacation Home in Deep Hole

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
United States
James E.
The price is ￥14,719
￥38,773 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Beach
Tangier Escape, great place get away from it all on Deal Island, MD.

Vacation Home in Deal Island Historic District

Tangier Escape, great place get away from it all on Deal Island, MD.
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is ￥14,817
￥31,743 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Tangier Escape, great place get away from it all on Deal Island, MD.
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

Cottage in Deal Island

Deal Island Bay Cottage
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is ￥22,319
￥40,688 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Deal Island Bay Cottage
Interior
Cozy cottage w/creekside fire pit & grill

Cottage in Up the Neck

Cozy cottage w/creekside fire pit & grill
9.4 out of 10, Exceptional, (137)
"Nice and quiet spot on island, kind of away from the busy parts of island. "
United States
Derek W.
The price is ￥31,210
￥58,212 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy cottage w/creekside fire pit & grill
Terrace/patio
Assateague Inn 104 by Seaside Vacations & Sales

Condo in Chincoteague Island

Assateague Inn 104 by Seaside Vacations & Sales
9.6 out of 10, Exceptional, (22)
"This was a great home-base as we trekked around Assateague and Chincoteague on our honeymoon. Very convenient to the Virginia side entrance to Assateague and the kitchen is perfect for breakfast and simple dinners. I was pleased to see the kitchen had everything you could need for basic cooking & there were a variety of drink glasses for both beer & wine!"
United States
Rosalynde V.
The price is ￥15,695
￥29,946 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Assateague Inn 104 by Seaside Vacations & Sales
Fridge, microwave, oven, stovetop
Salisbury Cottage

Vacation Home in Salisbury

Salisbury Cottage
10.0 out of 10, Exceptional, (34)
"House is fabulous very clean host are very responsive Great location Attended the annual Seagull Century and super convenient to the university Would definitely stay again Group from Pittsburgh "
United States
Donald T.
The price is ￥21,368
￥53,173 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Salisbury Cottage
Exterior
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Vacation Home in Birch Town

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
9.6 out of 10, Exceptional, (42)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is ￥16,377
￥62,706 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Interior
Only 5 min. from the Beach!

Condo in Chincoteague Island

Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (31)
"Great location that was very clean, kid friendly, and good amenities! Liked how close it was to everything, very walkable."
United States
Jeananne K.
The price is ￥15,695
￥29,946 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Only 5 min. from the Beach!
Exterior detail
The Neigh-Neigh - Location! Location! Location!

Vacation Home in Downtown Chincoteague

The Neigh-Neigh - Location! Location! Location!
10.0 out of 10, Exceptional, (4)
"House was clean, cozy and convenient for our weekend stay on the island. We will be there for the same event next year and will consider booking The Neigh Neigh again depending on who comes next time! Cheers"
United States
Bob S.
The price is ￥12,478
￥58,152 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Neigh-Neigh - Location! Location! Location!
Dining
Deluxe corner apartment with riverfront views close to dining and downtown

Apartment in Salisbury

Deluxe corner apartment with riverfront views close to dining and downtown
8.4 out of 10, Very Good, (5)
"It was seamless. Would stay here again."
United States
Joe C.
The price is ￥12,790
￥36,560 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Deluxe corner apartment with riverfront views close to dining and downtown
Terrace/patio
A Bargain on Chincoteague Island!

Condo in Chincoteague Island

A Bargain on Chincoteague Island!
8.8 out of 10, Excellent, (3)
"Overall the place was nice enough for the cost. "
United States
Stacey S.
The price is ￥15,695
￥29,771 total
includes taxes & fees
Jan 4 - Jan 5, 2026
A Bargain on Chincoteague Island!
Exterior detail
Salisbury Hideaway

Vacation Home in Salisbury

Salisbury Hideaway
10.0 out of 10, Exceptional, (20)
"This property was wonderful for our trip to Salisbury for my daughter's travel softball tournament. It was only 30-45 minutes from Ocean City (give or take traffic), and very close to many shopping areas and restaurants. The property itself was very clean and provided many necessities. "
United States
Lisa H.
The price is ￥18,248
￥50,175 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Salisbury Hideaway
TV
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Vacation Home in Snow Hill

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
2.0 star property
10.0 out of 10, Exceptional, (2)
"The hosts were wonderful, the house is beautiful, access & location was perfect. Next time I'm in the area & this place is avaliable, this is where I want to stay again. I recommend this house if you're in the area!!!Thanks to The Smiths"
United States
Sadat J.
The price is ￥20,354
￥32,928 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
Terrace/patio
The purple door at the bay.

Vacation Home in Captain's Cove

The purple door at the bay.
9.2 out of 10, Wonderful, (54)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is ￥24,565
￥70,105 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The purple door at the bay.
Smart TV, fireplace, table tennis, books
Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Vacation Home in Smith Island

Come escape to Smith Island for the winter and enjoy nature, peace and quiet
9.8 out of 10, Exceptional, (15)
"Such a lovely, cozy little house. Right in town. We could walk to restaurants and the bakery. We really enjoyed talking with the islanders and the walk out to Rhodes Point was beautiful. "
United States
Debra M.
The price is ￥28,075
￥45,135 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Property grounds
Only 5 min from Assateague National Seashore!

Condo in Chincoteague Island

Only 5 min from Assateague National Seashore!
7.4 out of 10, Good, (3)
"Low-quality furniture. needs to be updated"
United States
Susan E.
The price is ￥15,695
￥29,771 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Only 5 min from Assateague National Seashore!
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
"Great family stay. We stayed off-season (on purpose). This is a great Winter choice because of the relatively warm pool and nice hot tub. Good location as well with plenty to do nearby. Our room had a balcony with bay view. Hot breakfast. Clean, comfortable room and friendly staff."
Jeremy 2-night trip
Posted 2 days ago
Comfort Suites Chincoteague Island Bayfront Resort

Find out more about Westover

Search for holiday rentals in Westover on Expedia! You can easily find your home rentals, villas, holiday apartments in Westover using one of the methods below:

  • View our selection of featured holiday rentals in Westover
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Look no further and take a look at our great range of rental properties in Westover!

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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 Smart 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 4 vacation rentals for your stay in Westover.

What can I see and do in Westover?

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

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.