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Westover Holiday Rentals

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Check prices for these dates

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

Our top choices for Westover holiday 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, (63 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is AU$259
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$354
includes taxes & fees
26 Oct - 27 Oct
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
The price is AU$348
includes taxes & fees
27 Oct - 28 Oct
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.
The price is AU$387
includes taxes & fees
27 Sept - 28 Sept
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, (330 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is AU$323
includes taxes & fees
13 Oct - 14 Oct
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
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.
The price is AU$373
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$490
includes taxes & fees
27 Oct - 28 Oct
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.
The price is AU$454
includes taxes & fees
28 Sept - 29 Sept
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.
The price is AU$259
includes taxes & fees
28 Sept - 29 Sept
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, (647 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is AU$323
includes taxes & fees
18 Oct - 19 Oct
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
The price is AU$624
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$671
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$569
includes taxes & fees
26 Oct - 27 Oct
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.
The price is AU$298
includes taxes & fees
28 Sept - 29 Sept
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
The price is AU$493
includes taxes & fees
30 Sept - 1 Oct
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
The price is AU$471
includes taxes & fees
25 Oct - 26 Oct
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.
The price is AU$267
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$433
includes taxes & fees
30 Sept - 1 Oct
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, (35 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
The price is AU$278
includes taxes & fees
19 Oct - 20 Oct
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

Waterside Inn

Waterside Inn

8/10 Good
"have stayed here several times over the years and have always enjoyed our stay. the front desk people are always kind and helpful. the rooms are always clean the beds comfortable, and you have great views from the balcony. the problem is no ramp up to the office so if you have limited mobility such as i that is a major problem. also no rooms have handicap accessible tubs. we do love staying here but as i get older the issues with my mobility may not allow it."
LAWRENCE 3-night trip
Posted 11 hours ago
Waterside Inn

Find out more about Westover

Everything you need to know about Westover holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westover holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westover holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westover holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westover holiday rentals we have selected for you start as low as AU$278 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westover rentals

At Expedia, we put the best Westover holiday 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 holiday.

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. 

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 5 holiday 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 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.