Holiday Rentals in Chesapeake

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Holiday Rentals in Chesapeake

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very good, (1009)
"From checkin on, the staff was really friendly. The room was spacious and the kitchen well stocked. Gorgeous view of the Atlantic, right on the beach. Amole parking and walking distance to all of the shops in Va Beach. Loved it. "
The price is €151
includes taxes & fees
23 Mar - 24 Mar
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1296)
"Been here 3 times now and every time the staff is always helpful and just super nice. Overall just a really good team "
The price is €155
includes taxes & fees
23 Mar - 24 Mar
The Ocean Key Virginia Beach Resort

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1297)
"Great stay at a great price."
The price is €141
includes taxes & fees
23 Mar - 24 Mar
The Atrium Resort, Virginia Beach by Vacatia

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

9.8 out of 10, Exceptional, (98)
"Our family of 4 enjoyed a quiet time in the outer banks at this lovely beach house. November isn't exactly the time most folks visit the beach, but we've spent most of our lives in the far north, so the "chilly weather" didn't prevent us from enjoying kayaking in the inner channels and viewing the sunset from the crow's nest. We found the kitchen very adequate; we were able to cook a lovely thanksgiving dinner and ate quite well the entire time. We packed all our needs/food for the weekend so...
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (26)
"Great location, property is good for families as it has a full kitchen. It’s basic but at the beach you just need a property that is clean and in a good location. The mattress could definitely use updating. The fresh popcorn is a nice touch. There was an issue with my unit leaking down into the unit below while I was in the bath and maintenance had entered my unit . It could have been handled better instead of pounding on the bathroom door."
Four Sails Resort

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (64)
"Property was nice. But a little small."
The price is €234
includes taxes & fees
12 Mar - 13 Mar
The Art Door only minutes from beach

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

2.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect for our three families to spread out but also let the kids bunk up and enjoy downstairs all to themselves! We loved going down to the park, going to the market for donuts, walking the beach and enjoying the beautiful views. We can’t wait to stay here again next year. The house was well stocked, comfortable, and the host was very responsive to any questions.we loved it! "
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

Dolphin Run Oceanfront Suites Virginia Beach

4.5 star property
10.0 out of 10, Exceptional, (1)
"Condo was clean and close to everything. Staff was very friendly and helpful."
Dolphin Run Oceanfront Suites Virginia Beach

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

9.4 out of 10, Exceptional, (13)
"Great location and views. Property needs some updates and fixes. Good connectivity, TV's etc. We enjoyed our stay. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

Executive Oceanfront Retreat

7.8 out of 10, Good, (79)
"It was so quiet and so relaxing. I enjoyed the views and especially the ocean during the full moon! I believe if more investments are made many more will book this 90s vibe vacation home. This is definitely a vintage treasure and should be maintained but not toy changed. Lori is very communicative and I felt safe the entire time. Thank you for the stay."
Executive Oceanfront Retreat

Great Location ! 1 Short Block To The Boardwalk.

9.6 out of 10, Exceptional, (236)
"Condo was cute and comfortable. Close to the beach. Our first visit. Frank was great to work with. "
Great Location ! 1 Short Block To The Boardwalk.

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

10.0 out of 10, Exceptional, (41)
"Celebrated my mom’s 89th birthday with her 5 adult children and their spouses. The house was great. Very spacious and clean. Kitchen was stocked with everything you need to prepare meals for a large group. Man cave was wonderful. You could have a person comfortably stay in the man cave. House was great. "
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Beach Condo 2 Min Walk From The Beach

9.4 out of 10, Exceptional, (101)
"Charming & close to my parents Apartment "
Beach Condo 2 Min Walk From The Beach

Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

9.8 out of 10, Exceptional, (88)
"The condo is a refurbed motel room. Great location. Manager was quick to respond to questions_concerns. Cooking items were dirty and the sponge at the sink wrung out dirty water. Bathroom/shower were nicely redone. "
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

C9187 Leisure Dayz. Private 4x4 Beach Oceanfront Dream

9.4 out of 10, Exceptional, (3)
C9187 Leisure Dayz. Private 4x4 Beach Oceanfront Dream

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

9.8 out of 10, Exceptional, (165)
"Was awesome to get back to the beach, the house was amazing, and got to see the wild horses "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Best OBX vacation!4x4 beach, private dock, hot tub, pool, Horses. Pet-Friendly

10.0 out of 10, Exceptional, (3)
"Love love loved this place it was a great get away, the kids loved every minute of it and saw horses almost everyday even a baby one! Caught some fish from the dock and made lasting memories! Loved driving on the beach and not having to haul everything to it by hand! Would def recommend this for someone who doesn’t like the crowds and loves a real getaway to nature and beach! Kids can’t wait to go back!"
Best OBX vacation!4x4 beach, private dock, hot tub, pool, Horses. Pet-Friendly

The Mayflower - Luxury Beachside Penthouse #1602

3.4 out of 10, (6)
"Great location! One block off the beach with ocean views from almost every window--and there are a lot of windows providing great natural light during the day and views of city lights at night. Easy walk to restaurants, arts district, grocery store. The space is terrific for a large group. Two spacious seating areas provide separate areas for kids and adults. Amenities were sparse; so prepare for a trip to the store for essentials. Office management was courteous but inconsistent, at best, in...
The Mayflower - Luxury Beachside Penthouse #1602

VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool

2.0 star property
10.0 out of 10, Exceptional, (8)
"One of the nicest oceanside condos we've stayed in."
VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool

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

9.6 out of 10, Exceptional, (119)
"First time here to celebrate my 50th birthday Amazing location on the beach.House and host where amazing seeing the wild horses was a dream come true we will return thank you"
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
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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Other types of properties in Chesapeake you may be interested in

Wingate by Wyndham Chesapeake

2.5 star property
8.0 out of 10, Very good, (1021)
"Very nice staff"
The price is €74
includes taxes & fees
6 Apr - 7 Apr
Wingate by Wyndham Chesapeake

Comfort Suites Chesapeake - Norfolk

2.5 star property
8.2 out of 10, Very good, (1006)
"Room was clean just a minor issue with a dirty microwave."
The price is €78
includes taxes & fees
12 Mar - 13 Mar
Comfort Suites Chesapeake - Norfolk

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 star property
8.6 out of 10, Excellent, (1005)
"Front desk check in was one of the best Missing hard boiled eggs, guessing due to shortage "
The price is €109
includes taxes & fees
16 Mar - 17 Mar
Holiday Inn Express Chesapeake - Norfolk by IHG
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.

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?

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a patio 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. Make the most of table football in this rental home to help you unwind.

How many holiday rentals are there in Chesapeake?

Expedia has 39 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 Oak Grove Lake Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Virginia Beach Town Center and Naval Station Norfolk.

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.