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, (1434)
"Jimmy in Maintenance was awesome! We had to move to another room because toilet was leaking. Jimmy took care of everything even retrieving the keys to new room. The lady at the front desk requested we come down to get keys. Jimmy saw we were loaded with luggage and helped us tremendously!!!"
The price is €155
includes taxes & fees
17 Feb - 18 Feb
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Ocean Key Resort by VSA Resorts

3.0 star property
7.8 out of 10, Good, (1289)
"This was a great time "
The price is €141
includes taxes & fees
16 Feb - 17 Feb
The Ocean Key Resort by VSA Resorts

OBX Gorgeous 6BR beach house, stunning views . 4WD access. Wild Horses

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. "
OBX Gorgeous 6BR beach house, stunning views . 4WD access. Wild Horses

Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access

10.0 out of 10, Exceptional, (54)
"Would definitely stay here again! It was the perfect kitchen for a larger Thanksgiving meal and as a bonus, there were two fridges. The house was very clean with great access to the beach. From the second story, you can see the water. And of course, there were lots of horses."
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access

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

9.8 out of 10, Exceptional, (39)
"Found a spacious beautiful home. Did find the blender at the house broke due to the shaft being rounded out and exterior rear lights need cleaned and bulb changed. Also I'm my opinion 11 would be an easier check out time. We took 2 trash cans to the street as needed."
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (62)
"Friendly and inviting space. Great spot for our quick overnight stay. Definitely look at using again if need to return to the area."
The price is €244
includes taxes & fees
3 Feb - 4 Feb
The Art Door only minutes from beach

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1296)
"Great stay at a great price."
The Atrium Resort, Virginia Beach by Vacatia

Virginia Beach Oceanfront/Boardwalk, Beach, Pool & Balcony

10.0 out of 10, Exceptional, (48)
"This place is awesome. Clean, next to beach, and access to pool. Owners are super awesome to work with. "
Virginia Beach Oceanfront/Boardwalk, Beach, Pool & Balcony

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

{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

9.0 out of 10, Wonderful, (20)
"We enjoyed our visit. This house was very clean and the host was really helpful. "
The price is €330
includes taxes & fees
12 Feb - 13 Feb
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

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

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

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.

Oceanfront House on the beach at Croatan

8.2 out of 10, Very good, (103)
"We were not disappointed. I highly recommend "
Oceanfront House on the beach at Croatan

Dog-friendly home w/private pool and washer/dryer, WiFi, central AC, patio, deck

9.4 out of 10, Exceptional, (29)
"We stayed here for a small family reunion over Thanksgiving. The kitchen was well equipped for cooking a Thanksgiving dinner. I brought my own turkey roaster but everything else was provided. The rooms were spacious and comfortable. Of course the pool was closed in November but we would love to come back in the summer to enjoy the pool and the beach, which is a short walk. Overall I would recommend this property. "
Dog-friendly home w/private pool and washer/dryer, WiFi, central AC, patio, deck

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

Dolphin Run

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

Inviting oceanfront home with amazing views, private pool & deck

8.2 out of 10, Very good, (31)
"Positively beautiful view, excellent location, layout great. Bathrooms and Kitchen were clean and well maintained. Some suggestions: put a handrail at pool steps, vents,especially on wall in living room were filthy. Outside windows covered with bugs. Beach chairs and umbrella were all broken. For some reason hot water came out of both faucets in both masters. Minor changes would really enhance one’s stay but otherwise an enjoyable week."
Inviting oceanfront home with amazing views, private pool & deck

Semi-Oceanfront, Wild Horses, Pets Welcome, Private Pool, 4x2064, Happy Hours

9.0 out of 10, Wonderful, (7)
"The location of the house is great. We love the 4x4 beach so this was perfect. We had a bit of an issue with the cleaning when we first arrived but the cleaning team took care of everything the next day. The house is an older beach house but was overall a great place for our family get together. Looking to re-book for next year!"
Semi-Oceanfront, Wild Horses, Pets Welcome, Private Pool, 4x2064, Happy Hours

Breathtaking Ocean views at Pinch Me! 8bdrm, 6bath, private pool!

10.0 out of 10, Exceptional, (142)
"This is one of the cleanest and well equipped homes I have ever rented. The description and pics are completely accurate. Beds were comfy. Kitchen laid out well. Easy to communicate with the host and very responsive. Views incredible from inside and outside. Location was awesome - literally 60 steps and you are putting your beach chair down. SOO easy to come back and forth to the home. The decks offered beautiful views of the ocean and sunsets. I would 1000% rent this property again. 2...
Breathtaking Ocean views at Pinch Me! 8bdrm, 6bath, private pool!

Salty Anchor oceanfront sunrise Carova4WD only! Pets not allowed!

9.8 out of 10, Exceptional, (23)
"Perfect! Our short trip could have not been better. The house is equipped with everything we needed to host thanksgiving dinner. "
Salty Anchor oceanfront sunrise Carova4WD only! Pets not allowed!
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

Quality Inn

2.5 star property
5.8 out of 10, (638)
"I enjoyed my stay and I wasn’t bothered if I needed housekeeping I would let them know otherwise. It was a pleasant stay would stay again if I’m in the neighborhood. "
The price is €52
includes taxes & fees
23 Feb - 24 Feb
Quality Inn

Wingate by Wyndham Chesapeake

2.5 star property
8.0 out of 10, Very good, (1004)
"Hotel was fine, king bed comfy and spacious room with tub/shower microwave, fridge, coffee maker. Hot tub/pool was closed but that is okay."
The price is €92
includes taxes & fees
2 Mar - 3 Mar
Wingate by Wyndham Chesapeake

Aloft Chesapeake

3.0 star property
8.2 out of 10, Very good, (1004)
"The reception staff were very nice. "
The price is €100
includes taxes & fees
9 Feb - 10 Feb
Aloft Chesapeake
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?

Trendy home steps from beach access w/private outdoor pool, gas grill, balcony: This holiday home rental outside of Chesapeake is located near the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesapeake?

Expedia has 41 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 Great Dismal Swamp National Wildlife Refuge 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.