Search Vacation Homes in Westover

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Westover vacation homes

Dining
Cottage near the Bay

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52)
"Srea was quiet, peaceful, plenty of information provided about the area restaurants, grocery stores, etc. Enjoyed our stay."
United States
Darla J M.
$176 nightly
The price is $187
Dec 27 - Dec 28
Total with taxes and fees
Cottage near the Bay
Fridge, microwave, oven, stovetop
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
2.0 star property
Deep Hole
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.
$231 nightly
The price is $259
Jan 6 - Jan 7, 2026
Total with taxes and fees
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Fridge, microwave, oven, stovetop
Salisbury Cottage

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (34)
"Very clean, great communication and fabulous location close to SU!"
United States
Anne M.
$321 nightly
The price is $357
Dec 31 - Jan 1, 2026
Total with taxes and fees
Salisbury Cottage
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (66)
"Wonderful location. Walking distance to shops and restaurants and sunsets. Hosts were responsive and helpful. Check in and checkout were seamless."
United States
imelda s.
$254 nightly
The price is $285
Dec 24 - Dec 25
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Beach
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.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$194 nightly
The price is $206
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
Exterior
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

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, (42)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
$358 nightly
The price is $402
Dec 24 - Dec 25
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior detail
The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
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.
$358 nightly
The price is $402
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Neigh-Neigh - Location! Location! Location!
TV
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
2.0 star property
Snow Hill
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.
$189 nightly
The price is $209
Jan 3 - Jan 4, 2026
Total with taxes and fees
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
Exterior detail
Salisbury Hideaway

Salisbury Hideaway

Salisbury Hideaway
Salisbury
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.
$287 nightly
The price is $320
Jan 6 - Jan 7, 2026
Total with taxes and fees
Salisbury Hideaway
Terrace/patio
The purple door at the bay.

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (54)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
$408 nightly
The price is $449
Dec 24 - Dec 25
Total with taxes and fees
The purple door at the bay.
Fridge, microwave, oven, stovetop
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
Deep Hole
9.4 out of 10, Exceptional, (13)
"Went for a guys trip and enjoyed it "
United States
John W.
$389 nightly
The price is $437
Dec 24 - Dec 25
Total with taxes and fees
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
Smart TV, fireplace, table tennis, books
Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Smith Island
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.
$326 nightly
The price is $346
Dec 24 - Dec 25
Total with taxes and fees
Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Property grounds
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (60)
"The Property was very well-maintained and accommodating, with most everything you could need. This made the stay much simpler and more enjoyable. The dock and kayaks were a great addition to the fun. "
United States
Randy A.
$585 nightly
The price is $645
Jan 13 - Jan 14, 2026
Total with taxes and fees
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Westover Hotel Reviews

Waterside Inn

Waterside Inn

10/10 Excellent
"We have stayed here many times over the years and it is always a pleasant experience!"
Robyn 1-night trip
Posted 3 days ago
Waterside Inn

Find out more about Westover

Westover Vacation Homes information

Number of reviews
357
Accommodation
673 Vacation Homes
Lowest Price
$187
Highest Price
$645

Explore a world of travel with Expedia