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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Chesapeake

Indoor pool
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3.0 star property
Northeast Virginia Beach
7.8 out of 10, Good, (1451)
"Great stay, great recovery from other ocean front places! Great room for a family or girls sleepover!!"
United States
Aja-Brianne A
The Ocean Key Virginia Beach Resort
Terrace/patio
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1168)
"Staff was very attentive and welcoming! Very clean, such a great place!!"
United States
michelle
The price is ￥15,783
￥27,493 total
includes taxes & fees
Dec 7 - Dec 8
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Indoor pool
Four Sails Resort

Four Sails Resort

4.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (49)
"Sweet little spot for the price. Easy parking"
United States
Jon
The price is ￥16,245
￥20,649 total
includes taxes & fees
Nov 26 - Nov 27
Four Sails Resort
Terrace/patio
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.4 out of 10, Exceptional, (52)
"Excellent hotel. I will definitely stay there again. "
United States
Leta
The price is ￥18,688
￥21,461 total
includes taxes & fees
Nov 24 - Nov 25
stayAPT Suites Suffolk-Chesapeake
Exterior
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

Corolla
9.8 out of 10, Exceptional, (107)
"Place was great! Highly recommend!"
United States
Scott E.
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Property entrance
Angie's Guest Cottage

Angie's Guest Cottage

2.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (225)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
United States
Patricia
The price is ￥12,438
￥16,154 total
includes taxes & fees
Nov 23 - Nov 24
Angie's Guest Cottage
Smart TV, DVD player, books
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Corolla
9.6 out of 10, Exceptional, (125)
"Great place"
United States
Mike H.
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Fridge, microwave, oven, stovetop
Wildhorse Beachfront 12 bedroom Pool Estate

Wildhorse Beachfront 12 bedroom Pool Estate

Hatteras
8.4 out of 10, Very Good, (5)
"The house was beautiful and the experience with our family was perfect for the holidays. "
United States
Sean L.
Wildhorse Beachfront 12 bedroom Pool Estate
Property grounds
The Art Door only minutes from beach

The Art Door only minutes from beach

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.
The price is ￥15,688
￥36,234 total
includes taxes & fees
Nov 24 - Nov 25
The Art Door only minutes from beach
Smart TV, fireplace, video games, DVD player
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Corolla
9.8 out of 10, Exceptional, (186)
"Great house and location for a beach vacation"
United States
Tony B.
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Private kitchen
Luxurious RV

Luxurious RV

Sandbridge
8.4 out of 10, Very Good, (17)
"Had a great stay! Only wish that I would’ve booked an additional night. Would love to come back. "
United States
Heather M.
The price is ￥31,408
￥63,067 total
includes taxes & fees
Nov 22 - Nov 23
Luxurious RV
Property grounds
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

Corolla
9.6 out of 10, Exceptional, (65)
"The owner was extremely friendly and responsive. The location of the house was perfect- gorgeous views of the ocean, dunes and wild horses. Having a pool was also great for the entire family. This property had the perfect layout.We will be back!"
United States
Heather K.
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom
Pool
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Sandbridge
10.0 out of 10, Exceptional, (157)
"Fantastic location. Exactly as described. Perfect place for our family reunion. Hosts were very helpful and responded quickly to questions."
United States
Madeleine D.
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!
On the beach
C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!

C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!

2.0 star property
4x4 - Carova Beach
6.0 out of 10, (2)
"The house was located on a 4 x 4 only beach, which would have been fine if we had been informed prior to our arrival about the conditions to expect and the proper way to navigate them. We arrived after dark, during high tide, with inflated tires. We should have been told to watch the tide charts because the beach becomes impassable at high tide. We were not, and barely made it to our turn off because it was a shortly after high tide. We should have been told about letting the air out of the...
United States
William A.
C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!
Fridge, microwave, oven, stovetop
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

Dam Neck
9.4 out of 10, Exceptional, (107)
"Great location and amenities. Great access to the beach and it is in a very nice neighborhood."
United States
David H.
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Pool
Charming 2-bedroom apartment in fabulous Virginia Beach with WiFi, AC

Charming 2-bedroom apartment in fabulous Virginia Beach with WiFi, AC

Northeast Virginia Beach
9.0 out of 10, Wonderful, (12)
"Great spot close to the beach with parking for 2 vehicles. Host was very responsive and friendly. Will definitely stay again."
United States
David A.
Charming 2-bedroom apartment in fabulous Virginia Beach with WiFi, AC
A heated pool
C9703 12 BR 4X4 Oceanfront Luxury Retreat in Carova, Private Pool & Hot Tub - Prices Reduced!!

C9703 12 BR 4X4 Oceanfront Luxury Retreat in Carova, Private Pool & Hot Tub - Prices Reduced!!

Carova Beach
4.0 out of 10, (1)
"Home was in a great location with easy beach access and fantastic views. However, several issues included black mold on the mirrors in one bedroom, pool completely unfit for use, some bathrooms did not have any toilet paper at all, no bathrooms had any shampoo or hand soap (and this was not cautioned by the host), the couch showed visible stains (and it's on dark cloth), and the dishware was not clean. The host often took too long to respond (greater than 1-2 hours), so issues could not be...
United States
Viet N.
C9703 12 BR 4X4 Oceanfront Luxury Retreat in Carova, Private Pool & Hot Tub - Prices Reduced!!
Fridge, microwave, oven, stovetop
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Sandbridge
9.8 out of 10, Exceptional, (52)
"Great space, fab pool. Temp was excessively cold and difficult to regulate. Immaculately clean, great location. We loved Anchor Fown!!"
United States
Joyce L.
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Property grounds
Stunning oceanfront home with private indoor/outdoor pools, game room, theater

Stunning oceanfront home with private indoor/outdoor pools, game room, theater

Sandbridge
9.4 out of 10, Exceptional, (29)
"Had a great time at this beautiful spacious home for a family vacation. Room for everyone and the game room and pools were a huge hit. We would definitely go here again."
United States
Joyce F.
Stunning oceanfront home with private indoor/outdoor pools, game room, theater
A heated pool
Black Friday Sale: Oceanfront Mega-Estate | 14BR| Pool, Game Room, Wild Horses

Black Friday Sale: Oceanfront Mega-Estate | 14BR| Pool, Game Room, Wild Horses

Corolla
9.6 out of 10, Exceptional, (7)
"Despite there being some water issues towards the end of our trip, my family and I had a great time at this home. The space and amenities allowed everyone in the family, from the bookish to the sporty, to have an awesome time."
United States
Soraya H.
Black Friday Sale: Oceanfront Mega-Estate | 14BR| Pool, Game Room, Wild Horses
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

Schooner Inn

Schooner Inn

10/10 Excellent
"I love the Schooner Inn! I feel so comfortable there. I will be back in the near future!"
B 2-night trip
Posted 3 days ago
Schooner Inn

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Chesapeake. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best vacation home rentals in Chesapeake?

The Art Door only minutes from beach: This vacation home rental outside of Chesapeake comes with air-conditioning so you can feel at home during your trip.

How many vacation rentals are there in Chesapeake?

Expedia has 38 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Chesapeake City Park and Oak Grove Lake Park are a couple of great spots to enjoy the outdoors. Greenbrier Mall and Chesapeake Conference Center are other places to visit while you're in town.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.