Chesapeake Holiday Rentals

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Check prices for these dates

Tonight
17 Aug - 18 Aug
Tomorrow
18 Aug - 19 Aug
Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug

Holiday Rentals in Chesapeake

The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1433)
"My family has a really great time and stay"
The Atrium Resort, Virginia Beach by Vacatia
The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1418)
"Great views of the ocean, pizza spot was great for a quick bite, sunsations right next door, complimentary coffee machine in the lobby, and right across from Waterman’s which is a fantastic restaurant. Will definitely stay here again!"
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1122)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Four Sails Resort
Indoor pool

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (39)
"Great balcony with a great view"
Four Sails Resort
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (36)
"Excellent hotel. I will definitely stay there again. "
The price is HK$931
HK$1,069 total
includes taxes & fees
1 Sept - 2 Sept
stayAPT Suites Suffolk-Chesapeake
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (221)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
The price is HK$586
HK$765 total
includes taxes & fees
14 Sept - 15 Sept
Angie's Guest Cottage
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Smart TV, fireplace, video games, DVD player

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

9.8 out of 10, Exceptional, (178)
"This house was perfect for my family. The location was beautiful "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Smart TV, video games, DVD player, video library

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

8.4 out of 10, Very good, (21)
"I visited the Outer Banks with my daughters and honestly the stay was amazing, the views, house, location this place had it all. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (102)
"Lots of space and the third floor is a great place to hang out with a big group. Ocean is a quick walk away. But lots of things that we were expecting to be functional did not work. Upon arrival we were sent a message documenting a list of things that were broken, which was disappointing. The hot tub also turned out to be out of order. Still a good stay for a big group, but some love needs to be put into the house. "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Loft Space Minutes from Beach
Exterior

Loft Space Minutes from Beach

5.0 out of 10, (4)
"Overall the stay was good but they have a roach problem which in my opinion is very disgusting and would make me want to not stay here ever again. They also during our stay did not have functioning AC and just had a bunch of fans and a small mobile AC unit in the downstairs. Other than these two things it’s a very nice place and in a good convenient spot. "
Loft Space Minutes from Beach
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Smart TV, DVD player, books

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

9.6 out of 10, Exceptional, (121)
"We stayed at Lightly Salted last week; my family of five [2 adults, 3 kids (11, 5, 1)]and out close friends family of three [2 adults, 1 kid (3)]. "
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Nautical Dream, redecorated oceanfront home with incredible views and decks
On the beach

Nautical Dream, redecorated oceanfront home with incredible views and decks

10.0 out of 10, Exceptional, (12)
"Wonderful location, generous floor plan."
Nautical Dream, redecorated oceanfront home with incredible views and decks
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
Interior

Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

9.4 out of 10, Exceptional, (22)
"As listed close to everything and made our stay very easy. Communication with owner was easy and all questions we had were answered."
The price is HK$1,369
HK$3,354 total
includes taxes & fees
1 Sept - 2 Sept
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
Luxurious RV
Private kitchen

Luxurious RV

8.2 out of 10, Very good, (10)
"Upon arriving it was dark & I was having a hard time finding the residence. I gave the host a call & he was very friendly and helpful, was able to find it right after speaking with him. The RV is super cute, very relaxing view in the back."
The price is HK$1,565
HK$3,142 total
includes taxes & fees
19 Aug - 20 Aug
Luxurious RV
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!
Pool

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

10.0 out of 10, Exceptional, (152)
"With two adults and 16 high school seniors, this house was perfect! Enough big spaces to gather but enough smaller spaces to get away from the group. The pool was great and the location perfect. "
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse
Smart TV, fireplace, DVD player, books

OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

9.8 out of 10, Exceptional, (48)
"Wonderful trip with an awesome house. Very quiet and the house is beautiful. Lots of room. Thank you so much."
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse
Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach
Beach nearby, sun-loungers

Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

9.6 out of 10, Exceptional, (118)
"Great location and accomadations"
Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
On the beach, sun-loungers

Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

9.8 out of 10, Exceptional, (141)
"The house was beautiful, clean and plenty of room for all our guest! The view was amazing! "
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
The Art Door only minutes from beach
Property grounds

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (89)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is HK$782
HK$1,805 total
includes taxes & fees
25 Aug - 26 Aug
The Art Door only minutes from beach
Glamping your way-close to beach in Virginia Beach with AC
1 bedroom

Glamping your way-close to beach in Virginia Beach with AC

Glamping your way-close to beach in 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.
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Top Chesapeake Hotel Reviews

Oceans 2700

Oceans 2700

10/10 Excellent
"Great staff, clean room, nice pool and conveniently located a block from the beach"
Darryl 1-night trip
Posted 18 hours ago
Oceans 2700

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Broadmoor Play Area, or you can select a more secluded 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 holiday rentals that Chesapeake has to offer?

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chesapeake?

Expedia has 34 holiday 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 Crestwood Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Naval Station Norfolk and Sandbridge Beach.

What’s a holiday rental in Chesapeake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.