Search Vacation Homes in Chesapeake

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Vacation Homes in Chesapeake

Terrace/patio
3-bedroom home away from home in fabulous Chesapeake, Virginia.
3-bedroom home away from home in fabulous Chesapeake, Virginia.
2.0 star property
10.0 out of 10, Exceptional, (38)
"Very clean and welcoming I highly recommend "
United States
Christine G.
$207 nightly
The price is $241
Nov 15 - Nov 16
Total with taxes and fees
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Property grounds
Knot Three- Balcony View of ICW- Dog Friendly!
Knot Three- Balcony View of ICW- Dog Friendly!
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.
$198 nightly
The price is $223
Nov 4 - Nov 5
Total with taxes and fees
Knot Three- Balcony View of ICW- Dog Friendly!
Interior
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
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.
$225 nightly
The price is $254
Nov 5 - Nov 6
Total with taxes and fees
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
Property grounds
The Art Door only minutes from beach
The Art Door only minutes from beach
9.6 out of 10, Exceptional, (101)
"Loved our stay"
United States
TAMARA M.
$198 nightly
The price is $230
Nov 4 - Nov 5
Total with taxes and fees
The Art Door only minutes from beach
Dining
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach
8.8 out of 10, Excellent, (42)
"While we only stayed one night, we really enjoyed the property! It was super clean, located conveniently off of the highway, and communication with the owner was great! Would definitely stay there again! "
United States
Leisha S.
$304 nightly
The price is $352
Nov 4 - Nov 5
Total with taxes and fees
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach
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
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
$226 nightly
The price is $263
Nov 9 - Nov 10
Total with taxes and fees
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Fridge, microwave, oven, stovetop
Comfort near the water and University
Comfort near the water and University
7.0 out of 10, Good, (4)
"We had a nice stay. Thank you. "
United States
Rebecca S.
$265 nightly
The price is $299
Nov 10 - Nov 11
Total with taxes and fees
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!!
9.2 out of 10, Wonderful, (20)
"Amazing communication & response time with host. The house was clean and it was perfect for our trip! The neighborhood was a little crowded but it didn’t have an effect on us at all, just needed a place to stay. Thanks again!"
United States
lindsey c.
$248 nightly
The price is $288
Nov 11 - Nov 12
Total with taxes and fees
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Fridge, microwave, oven, stovetop
Beach Bungalow King Bed 1 Floor Living
Beach Bungalow King Bed 1 Floor Living
9.8 out of 10, Exceptional, (14)
"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.
$380 nightly
The price is $437
Nov 4 - Nov 5
Total with taxes and fees
Beach Bungalow King Bed 1 Floor Living
Fridge, microwave, oven, stovetop
Large 2 bedroom | Queen beds | Safe Area
Large 2 bedroom | Queen beds | Safe Area
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
$283 nightly
The price is $288
Nov 5 - Nov 6
Total with taxes and fees
Large 2 bedroom | Queen beds | Safe Area
Terrace/patio
Sojourn Aviators Dream on Back River
Sojourn Aviators Dream on Back River
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.
$420 nightly
The price is $447
Nov 11 - Nov 12
Total with taxes and fees
Sojourn Aviators Dream on Back River
Property grounds
10min to Ocean View: BBQ - Volleyball - Fire pit
10min to Ocean View: BBQ - Volleyball - Fire pit
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.
$309 nightly
The price is $358
Nov 30 - Dec 1
Total with taxes and fees
10min to Ocean View: BBQ - Volleyball - Fire pit
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
9.0 out of 10, Wonderful, (69)
"Excellent location just as described. Plan on reserving again and highly recommend."
United States
Mary W.
$247 nightly
The price is $287
Nov 4 - Nov 5
Total with taxes and fees
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Fridge, microwave, oven, stovetop
Old Beach House Made New Again, Enjoy the entire house.
Old Beach House Made New Again, Enjoy the entire house.
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
$354 nightly
The price is $410
Nov 4 - Nov 5
Total with taxes and fees
Old Beach House Made New Again, Enjoy the entire house.
Terrace/patio
Sojourn | Coastal Cottage | 3 BR
Sojourn | Coastal Cottage | 3 BR
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
$392 nightly
The price is $422
Nov 25 - Nov 26
Total with taxes and fees
Sojourn | Coastal Cottage | 3 BR
Microwave, stovetop, dishwasher, coffee/tea maker
*Midterm* Spacious Home at Buckroe Beach
*Midterm* Spacious Home at Buckroe Beach
2.0 star property
$492 nightly
The price is $501
Nov 4 - Nov 5
Total with taxes and fees
*Midterm* Spacious Home at Buckroe Beach
Fridge, microwave, dishwasher, coffee/tea maker
Cozy Condo Near Portsmouth Naval
Cozy Condo Near Portsmouth Naval
2.0 star property
$413 nightly
The price is $421
Nov 9 - Nov 10
Total with taxes and fees
Cozy Condo Near Portsmouth Naval
Microwave, oven, stovetop, dishwasher
Charming Beachside Retreat - Turtle
Charming Beachside Retreat - Turtle
2.0 star property
10.0 out of 10, Exceptional, (1)
"Thank you for the lil incredible paradise. House was clean with alot of rooms. PM was very welcoming and was always available to answer my questions."
United States
Andrew T.
$360 nightly
The price is $417
Nov 23 - Nov 24
Total with taxes and fees
Charming Beachside Retreat - Turtle
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!
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
$250 nightly
The price is $290
Nov 30 - Dec 1
Total with taxes and fees
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
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 Chesapeake Hotel Reviews

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent
"Great stay. Everything was wonderful. Clean. Staff was very friendly and helpful. Will be back."
Marissa 2-night trip
Posted 14 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
493
Accommodation
1415 Vacation Homes
Lowest Price
$223
Highest Price
$447

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