Search Vacation Homes in Chesapeake

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Chesapeake vacation homes

Terrace/patio

3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
The price is AED 559
AED 1,047 total
includes taxes & fees
14 Apr - 15 Apr
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Dining

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is AED 419
AED 1,500 total
includes taxes & fees
7 Apr - 8 Apr
Sojourn | Coastal Cottage | 3 BR
TV

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (110 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is AED 367
AED 847 total
includes taxes & fees
13 Apr - 14 Apr
The Art Door Duplex only minutes from beach
Fridge, microwave, oven, stovetop

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.4 out of 10, Exceptional, (29 reviews)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
The price is AED 436
AED 1,514 total
includes taxes & fees
9 Apr - 10 Apr
4 Bedroom Cottage - 5 Minutes from both beaches
Beach nearby, sun loungers, beach towels

Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (46 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is AED 478
AED 1,228 total
includes taxes & fees
7 Apr - 8 Apr
Cozy Beach Home in Oceanview
Outdoor dining

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
9.6 out of 10, Exceptional, (5 reviews)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is AED 388
AED 851 total
includes taxes & fees
14 Apr - 15 Apr
Knot Three- Balcony View of ICW- Dog Friendly!
Smart TV, fireplace, books, stereo

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
The price is AED 562
AED 1,942 total
includes taxes & fees
7 Apr - 8 Apr
Unique Luxurious Waterfront in Hampton
On the beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Willoughby Spit
8.8 out of 10, Excellent, (71 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AED 547
AED 1,054 total
includes taxes & fees
7 Apr - 8 Apr
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Exterior

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is AED 982
AED 2,011 total
includes taxes & fees
12 Apr - 13 Apr
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Smart TV

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"It’s was great staying "
United States
Shalena K.
The price is AED 367
AED 687 total
includes taxes & fees
4 May - 5 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Interior

Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is AED 516
AED 1,150 total
includes taxes & fees
14 Apr - 15 Apr
Large 2 bedroom | Queen beds | Safe Area
On the beach, sun loungers

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Willoughby Spit
8.8 out of 10, Excellent, (75 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is AED 511
AED 1,008 total
includes taxes & fees
7 Apr - 8 Apr
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Dining

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is AED 327
AED 987 total
includes taxes & fees
25 Apr - 26 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Interior

Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.6 out of 10, Exceptional, (29 reviews)
"We loved our stay here! The property is gorgeous, the rooms are bright and spacious, and the kitchen had everything we needed for a week long stay. The kids really loved being able to spend time in the back yard looking at the water and watching the jets fly overhead. Would definitely recommend and will rebook whenever we’re back in town! "
United States
Clare G.
The price is AED 808
AED 2,145 total
includes taxes & fees
9 Apr - 10 Apr
Sojourn Aviators Dream on Back River
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
7.6 out of 10, Good, (5 reviews)
"The host was welcoming, very clean, and quiet area. Ty"
United States
Hector S.
The price is AED 294
AED 1,087 total
includes taxes & fees
13 Apr - 14 Apr
Comfort near the water and University
Fridge, microwave, oven, stovetop

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Great stay, host is very responsive to issues and concerns "
United States
Jackson H.
The price is AED 367
AED 1,042 total
includes taxes & fees
22 Apr - 23 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Property grounds

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
8.8 out of 10, Excellent, (8 reviews)
"Great view and close to "
United States
Julian M.
The price is AED 547
AED 1,071 total
includes taxes & fees
7 Apr - 8 Apr
Beachfront Bungalow w/ BEST Location in Ocean View!
Dining

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (12 reviews)
"Easy check in. House very clean and well equipped. Comfortable stay"
United States
Nona C.
The price is AED 876
AED 2,100 total
includes taxes & fees
7 Apr - 8 Apr
Wooded Wonderland
Terrace/patio

Carrick Bend -Balcony View of ICW- Dog Friendly!

Carrick Bend -Balcony View of ICW- Dog Friendly!
Coinjock
8.0 out of 10, Very Good, (1 review)
The price is AED 726
AED 1,655 total
includes taxes & fees
12 Apr - 13 Apr
Carrick Bend -Balcony View of ICW- Dog Friendly!
Fridge, microwave, oven, stovetop

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
9.0 out of 10, Wonderful, (39 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is AED 613
AED 1,451 total
includes taxes & fees
7 Apr - 8 Apr
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
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 Chesapeake Hotel Reviews

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

8/10 Good
"The staff was amazing from check-in, maintenance (shower handle broken), extra towels to checkout. Restaurants and shopping were all close to hotel, even bike and beach rentals. Virginia Beach Coffee was a favorite, just across the street diagonally, owners and dog Dixie made the morning better!"
Carla 2-night trip
Posted 2 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel