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Search Vacation Homes in Chesapeake

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Dec 12 - Dec 14
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Jan 30 - Feb 1

Vacation Homes in Chesapeake

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

Vacation Home in Chesapeake

2.0 star property
10.0 out of 10, Exceptional, (39)
"Everything was great! "
United States
Nikki S.
$221 nightly
The price is $256
Dec 9 - Dec 10
Total with taxes and fees
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Beach nearby
Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.

Vacation Home in Corolla

9.8 out of 10, Exceptional, (16)
"Aaron and Kim were fabulous! From personal escorts at high tide to trips bringing a grill and charcoal. All members of my party were beyond impressed "
United States
Jacquie M.
$778 nightly
The price is $877
Dec 6 - Dec 7
Total with taxes and fees
Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.
Interior
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

Vacation Home in Coinjock

10.0 out of 10, Exceptional, (36)
"Cute, clean and well appointed. The view over the water is so pretty. We would stay again! "
United States
Susan H.
$229 nightly
The price is $259
Dec 4 - Dec 5
Total with taxes and fees
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
Property grounds
Knot Three- Balcony View of ICW- Dog Friendly!

Vacation Home in 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.
$198 nightly
The price is $223
Dec 4 - Dec 5
Total with taxes and fees
Knot Three- Balcony View of ICW- Dog Friendly!
Interior
New! Sandbridge Beach, 5bd/3Bth, Boat, Surf, Swim

Vacation Home in Sandbridge

9.4 out of 10, Exceptional, (3)
"Very clean- lots of spaces to relax - the game room was a HUGH hit with our teens! "
United States
Martha K.
$1,120 nightly
The price is $1,273
Dec 9 - Dec 10
Total with taxes and fees
New! Sandbridge Beach, 5bd/3Bth, Boat, Surf, Swim
TV, fireplace
New! VA Beach, 5bd/3Bth, Boat, Surf, Swim, Kayak

Vacation Home in Sandbridge

10.0 out of 10, Exceptional, (1)
"Family gathered for a wedding. Off-season so no pool or going to the beach (one street over). We loved the house and everything it offers!"
United States
Debrah M.
$1,048 nightly
The price is $1,189
Dec 4 - Dec 5
Total with taxes and fees
New! VA Beach, 5bd/3Bth, Boat, Surf, Swim, Kayak
Smart TV
NEW! Boat Ramp, Pool, Hot Tub

Vacation Home in Sandbridge

10.0 out of 10, Exceptional, (1)
$1,270 nightly
The price is $1,446
Dec 4 - Dec 5
Total with taxes and fees
NEW! Boat Ramp, Pool, Hot Tub
Smart TV, video games, foosball, table tennis
VB Paradise / Private Pool, Hot Tub

Vacation Home in Sandbridge

9.2 out of 10, Wonderful, (27)
"Enjoyable stay. Nice location. "
United States
Pamela H.
$1,158 nightly
The price is $1,324
Dec 4 - Dec 5
Total with taxes and fees
VB Paradise / Private Pool, Hot Tub
Terrace/patio
Designer 7BR w/ Pool and Hot Tub. Sleeps 20, Pets Welcome!

Vacation Home in Sandbridge

10.0 out of 10, Exceptional, (5)
"The house was perfect—great location close to the beach. We had a great time! Chris was always available to answer all questions in a timely manner. He took every opportunity to ensure a great stay. Looking forward to returning."
United States
Michael R.
$1,434 nightly
The price is $1,672
Dec 30 - Dec 31
Total with taxes and fees
Designer 7BR w/ Pool and Hot Tub. Sleeps 20, Pets Welcome!
Interior
Spacious 5BR + 2 Bonus Sleeping Rooms Beach Retreat| Private Pool, Hot Tub & Game Room

Vacation Home in Dam Neck

10.0 out of 10, Exceptional, (1)
"Perfect beach house for a big familyWe had a great stay! The house was in a perfect location just one block from the beach, spacious, and fit my family of 15 comfortably. There were plenty of beach chairs, wagons, and toys, which made it perfect for the whole family.The only small issue was limited towels (1 per person) and missing shampoo/body wash. The host was quick to respond and delivered body wash and shampoo early the next morning.Def recommend it to families looking for a spacious home...
United States
Ashley A.
$1,457 nightly
The price is $1,662
Dec 8 - Dec 9
Total with taxes and fees
Spacious 5BR + 2 Bonus Sleeping Rooms Beach Retreat| Private Pool, Hot Tub & Game Room
Beach
Your Perfect Beach Getaway! Gorgeous and spacious home perfect for a group!

Vacation Home in Northeast Virginia Beach

10.0 out of 10, Exceptional, (6)
"Very nice house, good location and easy to check in. My family really enjoyed staying there."
United States
Dan C.
$713 nightly
The price is $822
Dec 4 - Dec 5
Total with taxes and fees
Your Perfect Beach Getaway! Gorgeous and spacious home perfect for a group!
Sun loungers, beach towels
2 min walk to the beach! Gorgeous and spacious home perfect for a group!

Vacation Home in Northeast Virginia Beach

9.8 out of 10, Exceptional, (26)
"Excellent rental and location."
United States
James B.
$754 nightly
The price is $869
Dec 4 - Dec 5
Total with taxes and fees
2 min walk to the beach! Gorgeous and spacious home perfect for a group!
Fridge, coffee/tea maker, cookware/dishes/utensils, spices
TownHome 3blks Boardwalk

Vacation Home in Northeast Virginia Beach

10.0 out of 10, Exceptional, (5)
"We had the best time. The townhouse is perfect — plenty of space. Excellent layout. Location is PERFECT just a quick walk to the beach. Lots of restaurants nearby. Free parking. Bedrooms/ beds / bathrooms / kitchen all excellent. "
United States
Blythe T.
$245 nightly
The price is $284
Dec 4 - Dec 5
Total with taxes and fees
TownHome 3blks Boardwalk
Spices
Townhome 3 Blks from Boardwalk

Vacation Home in Northeast Virginia Beach

$257 nightly
The price is $298
Dec 4 - Dec 5
Total with taxes and fees
Townhome 3 Blks from Boardwalk
Interior
2 Bedroom Townhome 2 blks to VB Boardwalk

Vacation Home in Northeast Virginia Beach

8.0 out of 10, Very Good, (2)
"Beautiful with a homey feel. Great location and very clean. "
United States
Connie W.
$247 nightly
The price is $286
Dec 8 - Dec 9
Total with taxes and fees
2 Bedroom Townhome 2 blks to VB Boardwalk
Exterior
The Breaker House · *NEW* Spacious/Standalone 4BR Beach House

Vacation Home in Northeast Virginia Beach

10.0 out of 10, Exceptional, (21)
"Loved the location and the house was very clean. Beds were great too. Definitely would come back. "
United States
jamie h.
$775 nightly
The price is $851
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Breaker House · *NEW* Spacious/Standalone 4BR Beach House
Outdoor pool
Modernist Oasis is located in the beautiful North End of Virginia Beach

Vacation Home in Northeast Virginia Beach

9.8 out of 10, Exceptional, (9)
"We had a great time at the Modernist Oasis! Lots of space for our big family and great location. Hope to be back soon!"
United States
Imogen P.
$1,013 nightly
The price is $1,167
Dec 4 - Dec 5
Total with taxes and fees
Modernist Oasis is located in the beautiful North End of Virginia Beach
Property grounds
The Art Door only minutes from beach

Vacation Home in Northeast Virginia Beach

9.6 out of 10, Exceptional, (104)
"Great get away stay! Close drive to the shops and the beach. Very cozy. Would definitely stay there again!"
United States
Lizy G.
$197 nightly
The price is $228
Dec 4 - Dec 5
Total with taxes and fees
The Art Door only minutes from beach
Fridge, microwave, oven, stovetop
Comfort near the water and University

Vacation Home in Elizabeth city

7.0 out of 10, Good, (4)
"We had a nice stay. Thank you. "
United States
Rebecca S.
$265 nightly
The price is $299
Dec 8 - Dec 9
Total with taxes and fees
Comfort near the water and University
Exterior detail
New Beach Home on the Chesapeake Bay

Vacation Home in East Ocean View

8.8 out of 10, Excellent, (3)
"Excellent Host! The check in process an eaze! The house is as described super clean! The host provided more than enough accommodations and even leaves a nice treat for their guest! The location is excellent right by the stairs to the beach! Will definitely book again. "
United States
Shardae F.
$704 nightly
The price is $813
Dec 7 - Dec 8
Total with taxes and fees
New Beach Home on the Chesapeake Bay
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

Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent
"The room was very comfortable. "
RICKY 2-night trip
Posted 1 day ago
Comfort Inn & Suites Hampton near Coliseum

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
307
Accommodation
1390 Vacation Homes
Lowest Price
$223
Highest Price
$1,672

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