Search Holiday Rentals in Chesapeake

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Top Holiday Rentals in Chesapeake

The Atrium Resort by VSA Resorts
Interior
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very good, (1065)
"everything about the hotel was amazing. i had a few negative experiences here, one being that the water in the shower seemed to be broken, could only have burning hot or freezing cold water, and then if i did get hot water it would only be hot for about 5 minutes before it was freezing again. the parking was great, distance from restaurants and other activities was amazing, very clean room and common areas. also the tv in the living area of the suite seemed to have issues as well because having...
The price is £116
per night
5 May - 6 May
The Atrium Resort by VSA Resorts
The Ocean Sands Resort by VSA Resorts
Exterior
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very good, (1252)
"The staff was very friendly and courteous. The room was nice, oceanview waz lovely! The only complaint was the parking, it wasn't any ample space but we managed to find a spot.. We will definitely be back. Thank you for courtesy, kindness and sincerity!"
The price is £166
per night
16 May - 17 May
The Ocean Sands Resort by VSA Resorts
The Ocean Key Resort by VSA Resorts
Indoor pool
The Ocean Key Resort by VSA Resorts
3.0 star property
7.6 out of 10, Good, (1114)
"Game room with pool table "
The price is £134
per night
15 May - 16 May
The Ocean Key Resort by VSA Resorts
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Beach Condo 2 Min Walk From The Beach
Beach
Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, (91)
"This condo was absolutely fabulous. It is literally 2 minute walk to the beach access. The rooms were comfortable and I've never stayed at a Vrbo with such an impressively stocked kitchen. The host responded quickly and answered all our questions. They were also very responsive. It was a lovely stay."
Beach Condo 2 Min Walk From The Beach
Beach Condo, Walk To The Beach
Beach | Beach nearby
Beach Condo, Walk To The Beach
9.4 out of 10, Exceptional, (40)
"The property owner felt like a longtime friend by the time our weekend was over. Super nice & welcoming. The place was perfect for what we needed. The shower was a little small but thats just bc we needed more. Its perfect for a small family stay. Thank you for allowing us to be there. You are awesome!"
Beach Condo, Walk To The Beach
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
Outdoor pool, a heated pool
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
10.0 out of 10, Exceptional, (37)
"The home enabled us to enjoy our stay in the Outer Banks. We were unfamiliar with the area and the 4X4 beach driving, but love learning new things. The weather was not the best, but with the comforts of the home, we were had a relaxing time playing games, enjoying the hot tub and binge watching TV. The place is quite clean. And I am very picky about that. So thank you for ensuring a comfortable stay."
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
Cozy Suite at the Beach
On the beach, sun-loungers
Cozy Suite at the Beach
8.4 out of 10, Very good, (53)
"We had a great stay at this property for 3 nights. It is a perfect fit for two adults and a dog and was right around the corner from the ocean. The bed and bathtub were absolutely wonderful! I appreciated the communication from owners and had an easy, peaceful weekend. Thanks!"
The price is £257
per night
6 May - 7 May
Cozy Suite at the Beach
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Fridge, microwave, oven, stovetop
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
9.8 out of 10, Exceptional, (29)
"The house itself was nice, clean although slightly in need of updates in the kitchen."
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
On the beach, sun-loungers, beach towels
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
10.0 out of 10, Exceptional, (64)
"We were in town for Shamrock Marathon weekend and found the location absolutely perfect. The race start area is right outside the door. Although we didn't use the kitchen, it seemed well stocked with utensils, tools, etc and would have been ok for an extended stay. The unit was clean, the bed was very comfortable, the shower was nice and had plenty of hot water. We took one star off for cleanliness because the sofa is a little stained. We tossed a blanket on it however and it was fine. The pool...
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
Angie's Guest Cottage
Property entrance
Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (177)
"Honestly the only negative was the tiny parking space but it's beachfront cottage. having parking included at all was nice. Friendly clean and close to everything"
The price is £93
per night
5 May - 6 May
Angie's Guest Cottage
Great Location ! 1 Short Block To The Boardwalk.
Beach nearby, sun-loungers
Great Location ! 1 Short Block To The Boardwalk.
9.6 out of 10, Exceptional, (203)
"Our stay was wonderful! Place was nice, clean, and provided everything we needed for our stay. This location is right in the heart of Virginia Beach! There were tons of things to do, go, and eat! There was tons of shopping also! Frank sent me everything I needed for check in and his responses were quick!! I will stay here again when I come back!"
Great Location ! 1 Short Block To The Boardwalk.
Lovely 4-bedroom open concept home 8mins from oceanfront
Private kitchen
Lovely 4-bedroom open concept home 8mins from oceanfront
2.0 out of 10, (2)
"I am not sure where to begin. The water was shut off for non-payment and the host tried to say it was due to work. There were bugs. The dishwasher was full of dishes which may have been washed but were definitely not clean. The bathroom had used toothbrushes in a container on the counter. Someone had been on one of the beds prior to our check in. A pillow had blood on it. The couch had uses tissues under the pillows. I can go on! This property is completely misrepresented! If you are going to...
Lovely 4-bedroom open concept home 8mins from oceanfront
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Beach | On the beach, sun-loungers
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
8.4 out of 10, Very good, (37)
"The ceiling was low, bathroom sink was clogged. Bathroom floor needs work. Property was clean and beds were comfortable. Loved being at the beach. They have a different Property i stayed at on an earlier date that was great. Although we didnt care for the mentioned things, the process was easy and the owners were good to deal with."
The price is £290
per night
6 May - 7 May
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Norfolk Beach Cottage Rental
Sun-loungers, beach towels
Norfolk Beach Cottage Rental
9.0 out of 10, Wonderful, (225)
"What a lovely home. Great for the whole family. Hosts were wonderful at communication with us throughout the weekend. Loved how close the beach was an easy to get to lots of restaurants etc. Kitchen was well stocked and plenty of seating in the dining room and comfy living area. I hope we can return if my daughter goes to ODU"
The price is £323
per night
6 May - 7 May
Norfolk Beach Cottage Rental
Sunrises on the beach & sunsets on the bay! Stay at Starfish Bay!
Beach nearby, sun-loungers
Sunrises on the beach & sunsets on the bay! Stay at Starfish Bay!
9.6 out of 10, Exceptional, (18)
"Very cute little place for a couple located on the bay one block from the ocean. Harriet was amazing. I had the best customer service experience with her. Bed was a little small but comfortable (definitely allowed for cuddling)and water pressure in the shower was low, but that is a self preference. If available we would absolutely stay again."
Sunrises on the beach & sunsets on the bay! Stay at Starfish Bay!
Newly Renovated, Pet-Friendly 1st FLR 2 BR Cottage by Boardwalk (508A)
Exterior
Newly Renovated, Pet-Friendly 1st FLR 2 BR Cottage by Boardwalk (508A)
9.0 out of 10, Wonderful, (30)
"Great location, easy access to both the beach and the Sport Center, and. Farmer’s market popped up on Saturday just a block away. Great stay!"
Newly Renovated, Pet-Friendly 1st FLR 2 BR Cottage by Boardwalk (508A)
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Beach nearby, sun-loungers
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
9.0 out of 10, Wonderful, (47)
"House was old (as described) and a bit shabby but very clean. Even a few minimal upgrades would improve it immensely. However the price was right and the location for that price was great! The fishing pier with the restaurant/bar at the end was a bonus. Beautiful beach to walk. The weather did not cooperate with us - we were a week too early but you can’t change the weather!"
The price is £291
per night
6 May - 7 May
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
SPRING SPECIAL !!!Canal Front - Paddle Board
Smart TV, fireplace
SPRING SPECIAL !!!Canal Front - Paddle Board
9.8 out of 10, Exceptional, (30)
"We had a great week. Kevin was great and help us out when we needed it."
SPRING SPECIAL !!!Canal Front - Paddle Board
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Beach nearby
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
9.0 out of 10, Wonderful, (42)
"We have family in Norfolk! That would be a great rental in the summer months."
The price is £291
per night
6 May - 7 May
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Skyview by the Sea
Property grounds
Skyview by the Sea
Skyview by the Sea
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See all available properties in 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.

Other types of properties in Chesapeake you may be interested in

Comfort Suites Chesapeake - Norfolk
Suite, 1 King Bed with Sofa bed | Individually decorated, individually furnished, desk, laptop workspace
Comfort Suites Chesapeake - Norfolk
2.5 star property
8.2 out of 10, Very good, (1002)
"Though the parking lot was having work done, you would have never known it coming into the hotel. We were welcomed with a smile. Our room was clean, hallways quite. We all had a very good night sleep. Breakfast was good, everything was hot. Coffee was amazing. I would definitely stay here again."
The price is £94
per night
19 May - 20 May
Comfort Suites Chesapeake - Norfolk
Wingate by Wyndham Chesapeake
Lobby lounge
Wingate by Wyndham Chesapeake
2.5 star property
8.0 out of 10, Very good, (1003)
"The hotel was well kept great indoor pool and whirlpool pool the staff was amazing and the breakfast was great also plenty of parking "
The price is £138
per night
5 May - 6 May
Wingate by Wyndham Chesapeake
Fairfield Inn and Suites By Marriott Chesapeake
Room, 1 King Bed | Desk, laptop workspace, blackout curtains, iron/ironing board
Fairfield Inn and Suites By Marriott Chesapeake
2.5 star property
8.8 out of 10, Excellent, (790)
"Nice hotel"
The price is £99
per night
19 May - 20 May
Fairfield Inn and Suites By Marriott 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.

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as £93 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Jillian's Billiards, 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?

The Atrium Resort by VSA Resorts: This holiday home rental outside of Chesapeake is located by the ocean, and has an indoor pool, an arcade/games room and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Chesapeake?

Expedia has 35 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Great Dismal Swamp National Wildlife Refuge and Oak Grove Lake Park are a couple of scenic spots to enjoy the outdoors, whereas Portlock Galleries at SoNo is one of the cultural attractions. 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.

Recent reviews of Chesapeake properties
Expedia verified reviews

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

5/5 Excellent
"I enjoyed the easy access to the beach and boardwalk. I did not like the lack of parking, forced to valet car."
A verified traveller stayed at Hyatt Place Virginia Beach / Oceanfront
Posted 13 hours ago
Hyatt Place Virginia Beach / Oceanfront