Colorful sunset over riverside resort in Cambridge Maryland USA

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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesapeake vacation homes

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, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
3-bedroom home away from home in fabulous Chesapeake, Virginia.

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
8.4 out of 10, Very Good, (6 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 516
AED 1,046 total
includes taxes & fees
16 Jun - 17 Jun
Knot Three- Balcony View of ICW- Dog Friendly!

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, (5 reviews)
"Quiet comfortable"
United States
Rebecca K
The price is AED 294
AED 975 total
includes taxes & fees
17 Jun - 18 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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, (28 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is AED 408
AED 1,113 total
includes taxes & fees
29 Jun - 30 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

bedroom house in charming E City perfect for relaxing

bedroom house in charming E City perfect for relaxing
Elizabeth City
The price is AED 337
AED 589 total
includes taxes & fees
6 Jul - 7 Jul
bedroom house in charming E City perfect for relaxing

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
9.4 out of 10, Exceptional, (6 reviews)
"It’s was great staying "
United States
Shalena K.
The price is AED 551
AED 911 total
includes taxes & fees
16 Jun - 17 Jun
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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 643
AED 1,443 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Beach Home in Oceanview

Perfect Beach Getaway for 5! Steps to the Sand!

Perfect Beach Getaway for 5! Steps to the Sand!
Buckroe Beach
9.6 out of 10, Exceptional, (27 reviews)
"We had a very nice stay."
United States
Rod S.
The price is AED 694
AED 1,638 total
includes taxes & fees
10 Jul - 11 Jul
Perfect Beach Getaway for 5! Steps to the Sand!

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, (77 reviews)
"Clean, cozy, well prepared.Location!!!"
United States
Caleb J.
The price is AED 823
AED 1,426 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
The price is AED 783
AED 1,643 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is AED 628
AED 2,022 total
includes taxes & fees
16 Jun - 17 Jun
Unique Luxurious Waterfront in Hampton

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very Good, (7 reviews)
"Everything was wonderful"
United States
Marc
The price is AED 331
AED 1,104 total
includes taxes & fees
16 Jul - 17 Jul
Comfort near the water and University

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is AED 579
AED 1,479 total
includes taxes & fees
21 Jun - 22 Jun
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

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 919
AED 1,910 total
includes taxes & fees
7 Jul - 8 Jul
Carrick Bend -Balcony View of ICW- Dog Friendly!

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
9.2 out of 10, Wonderful, (18 reviews)
"George was a very responsive host. Great beachfront location. Very comfortable relaxing setting. Will definitely be back!!! "
United States
Carter S.
The price is AED 823
AED 1,443 total
includes taxes & fees
17 Jun - 18 Jun
Beachfront Bungalow w/ BEST Location in Ocean View!

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 364
AED 973 total
includes taxes & fees
16 Jun - 17 Jun
Large 2 bedroom | Queen beds | Safe Area

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 2,007 total
includes taxes & fees
16 Jun - 17 Jun
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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, (75 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AED 951
AED 1,599 total
includes taxes & fees
16 Jun - 17 Jun
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!

-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
Newport News
9.8 out of 10, Exceptional, (11 reviews)
"Everything was very clean good coffee options plenty of hot water :)"
United States
Allen C.
The price is AED 1,466
AED 2,221 total
includes taxes & fees
30 Jun - 1 Jul
-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!

Cozy 1-bedroom apartment in beautiful Virginia Beach with AC

Cozy 1-bedroom apartment in beautiful Virginia Beach with AC
Northeast Virginia Beach
The price is AED 1,322
AED 1,976 total
includes taxes & fees
16 Jun - 17 Jun
Cozy 1-bedroom apartment in beautiful Virginia Beach with AC
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Hotel Reviews