Search Vacation Homes in Chesapeake

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

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chesapeake

3-bedroom house in Chesapeake with workspace, ready-to-cook kitchen, and yard

2.0 star property
Chesapeake
3-bedroom house in Chesapeake with workspace, ready-to-cook kitchen, and yard

10min to Ocean View: BBQ - Volleyball - Fire pit

Norfolk
10.0 out of 10, Exceptional, (1)
"Very nice property to stay at plenty to do staying there. Good location plenty of places around for anything you may need. Host was nice and available to answer any questions I had. Would love staying there again sometime!"
United States
Zachary C.
The price is AED 361
AED 1,212 total
includes taxes & fees
11 Nov - 12 Nov
10min to Ocean View: BBQ - Volleyball - Fire pit

Knot Three- Balcony View of ICW- Dog Friendly!

Coinjock
9.6 out of 10, Exceptional, (4)
"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 349
AED 828 total
includes taxes & fees
11 Nov - 12 Nov
Knot Three- Balcony View of ICW- Dog Friendly!

Comfort near the water and University

Elizabeth city
7.0 out of 10, Good, (4)
"We had a nice stay. Thank you. "
United States
Rebecca S.
The price is AED 294
AED 1,079 total
includes taxes & fees
17 Nov - 18 Nov
Comfort near the water and University

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

Portsmouth
9.6 out of 10, Exceptional, (4)
"Great little home away from home. Came to visit my granddaughter that's in the Navy. Nice place to just sit and play games and visit. Couldn't get in at first but the owners answered the phone and took care of it right away. Would definitely stay here again!"
United States
Anonymous traveler
The price is AED 294
AED 966 total
includes taxes & fees
21 Nov - 22 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

Coinjock
10.0 out of 10, Exceptional, (36)
"Quiet, great views, great property and dock, overall amazing experience for me and my family."
United States
Aiden P.
The price is AED 404
AED 953 total
includes taxes & fees
4 Dec - 5 Dec
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

Virginia Beach
8.8 out of 10, Excellent, (42)
"Beautiful Home! Easy Check-In/Check-Out! Everything you could need is right on premises. Just bring your food and drinks. "
United States
Jessica W.
The price is AED 463
AED 1,291 total
includes taxes & fees
16 Nov - 17 Nov
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.

Corolla
9.8 out of 10, Exceptional, (16)
"Overall best experience to date I’ve had at OBX. Raw and untamed, what I envisioned the island to be before heavy tourism and development. Wild horse encounters were more than you can count on two hands! Trent and Stephanie were helpful,prompt,and courteous.private and secluded ."
United States
Cameron S.
The price is AED 496
AED 3,230 total
includes taxes & fees
11 Nov - 12 Nov
Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.

The Art Door only minutes from beach

Northeast Virginia Beach
9.6 out of 10, Exceptional, (103)
"This is a lovely little spot that had just enough room for us! The parking situation was a bit confusing but Garrett responded quickly and was very helpful. We had everything we needed for our stay."
United States
Melissa Y.
The price is AED 367
AED 852 total
includes taxes & fees
19 Nov - 20 Nov
The Art Door only minutes from beach

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

Portsmouth
9.2 out of 10, Wonderful, (20)
"House was clean and welcoming. Communication was great. I would stay again in a heart beat. I’m active duty military and host was very accommodating. "
United States
Kristen H.
The price is AED 367
AED 1,059 total
includes taxes & fees
11 Nov - 12 Nov
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Beach Bungalow King Bed 1 Floor Living

Bayview
9.8 out of 10, Exceptional, (15)
"The house is located in a nice quiet neighborhood and is a 3 to 5 minute walk to the beach. The beach was never crowded and clean. The house was very cleaned and well maintained."
United States
Daniel G.
The price is AED 595
AED 1,625 total
includes taxes & fees
11 Nov - 12 Nov
Beach Bungalow King Bed 1 Floor Living

Sojourn | Coastal Cottage | 3 BR

Willoughby Spit
9.4 out of 10, Exceptional, (34)
"Our stay was fantastic! Great location, close to beach and bay, close to grocery store, and only about 20-25min from VA Beach. "
United States
rosetta
The price is AED 459
AED 1,513 total
includes taxes & fees
25 Nov - 26 Nov
Sojourn | Coastal Cottage | 3 BR

Old Beach House Made New Again, Enjoy the entire house.

Norfolk
8.8 out of 10, Excellent, (29)
"House was very spacious and clean. Updated and nice. Communication was A1 and as expected from listing. Extremely happy with overall experience. "
United States
FaT_ KId203
The price is AED 474
AED 1,527 total
includes taxes & fees
11 Nov - 12 Nov
Old Beach House Made New Again, Enjoy the entire house.

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

Willoughby Spit
9.0 out of 10, Wonderful, (71)
"Like the fire pit outside and so close to the beach and the pier the only downside is 1 bedroom doesn’t have AC but other than that it’s perfect We’ll stay there again "
United States
mimi i
The price is AED 474
AED 970 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

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

Willoughby Spit
9.0 out of 10, Wonderful, (69)
"Location was amazing and made the house worthwhile "
United States
Misti W.
The price is AED 511
AED 1,020 total
includes taxes & fees
16 Nov - 17 Nov
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Sojourn Aviators Dream on Back River

Fox Hill
9.6 out of 10, Exceptional, (27)
"My family enjoyed the experience of staying near the water. The views were lovely! "
United States
Precious E.
The price is AED 440
AED 1,632 total
includes taxes & fees
11 Nov - 12 Nov
Sojourn Aviators Dream on Back River

Charming 3bd - Near beaches - Foosball & Backyard

2.0 star property
Bayview
9.4 out of 10, Exceptional, (3)
"A great house in a quiet neighborhood. We were a short walk to the beach. Plenty of great restaurants within walking or a short drive. The house was recently renovated and was in great condition. We would stay again. "
United States
Matt D.
The price is AED 503
AED 1,544 total
includes taxes & fees
16 Nov - 17 Nov
Charming 3bd - Near beaches - Foosball & Backyard

Large 2 bedroom | Queen beds | Safe Area

Wythe
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is AED 408
AED 1,034 total
includes taxes & fees
11 Nov - 12 Nov
Large 2 bedroom | Queen beds | Safe Area

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cottage Park
9.6 out of 10, Exceptional, (5)
"We had a wonderful stay in this cute and cozy cottage! The space had such a charming vibe, perfect for relaxing. The shower was absolutely amazing—definitely a highlight. There was plenty of room for additional family members to join us for a fun game night, which made the stay even more special. The long, narrow driveway provided adequate parking, which was super convenient. We also loved exploring the local eateries—AJ Gators had delicious gator bites, and Karla’s Beach House served up a...
United States
Vandisha B.
The price is AED 603
AED 1,743 total
includes taxes & fees
11 Nov - 12 Nov
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cozy Condo Near Portsmouth Naval

2.0 star property
Portsmouth
The price is AED 518
AED 1,546 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Condo Near Portsmouth Naval
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