Chesapeake Vacation Rentals

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Vacation Rentals in Chesapeake

Outdoor pool, a heated pool
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
10.0 out of 10, Exceptional, (39)
"Our family had a wonderful stay! We loved the remoteness of the house and the easy walk to the beach. The heated pool was perfect even though it was a chilly week. We can't wait to return!"
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
On the beach, sun loungers, beach towels
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
10.0 out of 10, Exceptional, (65)
"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
Outdoor dining
Entire home on Bells Island in Currituck County NC
10.0 out of 10, Exceptional, (3)
"Excellent option for my duck hunting crew. Lots of space, outstanding kitchen with everything you need."
Entire home on Bells Island in Currituck County NC
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Property grounds
Oceanfront Luxury Home w/ Private Pool, Hot Tub, Game Room & More!
10.0 out of 10, Exceptional, (19)
"This property was an absolute dream. The house was gorgeous and had every amenity you could think of. The location and the view of the ocean was breathtaking. We saw dolphins and the horses came right up to the house on more than one occasion! Even the beach driving was a fun experience that I already miss. Will happily book at the Seashine in the years to come."
Oceanfront Luxury Home w/ Private Pool, Hot Tub, Game Room & More!
Property grounds
The Art Door only minutes from beach
9.8 out of 10, Exceptional, (36)
"This cute little apartment is the perfect getaway spot and pet friendly! It was super clean and smelled fantastic. The fenced in backyard is perfect to just sit out and enjoy the warm weather, and to be outside with your dog! The bathroom is a great size and beautiful! The bed was very comfortable and the linens and towels were great quality. The living room and kitchen was an added bonus, although we didn’t use it much. The host was very responsive and attentive to our needs, offering to adjust...
The price is CA $164
CA $353 total
includes taxes & fees
Jun 11 - Jun 12
The Art Door only minutes from beach
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
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
3 bedrooms, desk, iron/ironing board, travel crib
Norfolk Oasis
9.8 out of 10, Exceptional, (10)
"From the moment we walked in the door we were immediately greeted with the smell of freshly cleaned floors, linens, and counter tops. I was very impressed by the customer service of our hosts and the speed at which they responded to any of our questions. They were very kind and respectful as well. We were visiting from NY, and the house was pleasantly bigger than what we expected. They provided clean linens and basically everything we needed for the weekend. Will definitely recommend and stay...
Norfolk Oasis
Beach nearby, sun loungers
Great Location ! 1 Short Block To The Boardwalk.
9.6 out of 10, Exceptional, (204)
"Great communication when I had trouble getting code to get in. Very clean. We were there for volleyball tournament so short stay and didn’t cook. My only feedbacks are minor. Pillows not great so hate this one time I didn’t bring mine. Toilet paper is thin. Parking is tight. I don’t know how I’d of gotten out it lot full."
The price is CA $376
CA $715 total
includes taxes & fees
Jun 9 - Jun 10
Great Location ! 1 Short Block To The Boardwalk.
Terrace/patio
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
9.6 out of 10, Exceptional, (78)
"We are Senior Citizens that rent this property a couple times a year in the off season to visit our son and his family in Virginia Beach. The property is always clean and well kept. It is fully equipped with everything we need. All appliances and heating work well. The neighborhood is quiet and is only a 10 -15 minute drive to good restaurants on Shore Drive. We always enjoy our stay at this location near Fort Story."
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Lake
Pet-Friendly Cottage in Amenity-Filled Currituck Sound Campground (J04)
9.6 out of 10, Exceptional, (23)
"Very clean, comfortable, fun activities available, great location on the sound. "
Pet-Friendly Cottage in Amenity-Filled Currituck Sound Campground (J04)
Property grounds
OBX Gorgeous 6BR beach house, stunning views . 4WD access. Wild Horses
9.6 out of 10, Exceptional, (8)
"Very nice area."
OBX Gorgeous 6BR beach house, stunning views . 4WD access. Wild Horses
Beach
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
Fridge, microwave, oven, stovetop
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
9.4 out of 10, Exceptional, (78)
"Great house and location for a family gathering."
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia 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
Exterior
Newly Renovated, Pet-Friendly 1st FLR 2 BR Cottage by Boardwalk (508A)
9.2 out of 10, Wonderful, (31)
"We chose this property due to its central location that allowed us to enjoy the oceanfront within a 5 minute walk and the VIBE Arts district just steps from the front (or back) door. Location was also a short drive to the Virginia Aquarium, First Landing State Park, & Back Bay Nat'l Wildlife refuge. Our family of 3 stayed 4 nights. Loved exploring the eateries, shops, and art of the VIBE district by foot...not to mention the brewery across the street! Loved walking to oceanfront for early AM...
Newly Renovated, Pet-Friendly 1st FLR 2 BR Cottage by Boardwalk (508A)
Sun loungers, beach towels
Norfolk Beach Cottage Rental
9.0 out of 10, Wonderful, (226)
"This place was placed perfectly. Just across the street from a very nice peaceful beach access, as well as a large park for children and dogs. There was an exceptional farmers market on Saturday that had an immense variety of local product and food trucks. The hosts were very responsive and accommodating. My family and I stayed (Grandma 72 years old, aunts and cousins from 6years old to 37, and my mother 52 years old.) I would stay here again."
The price is CA $272
CA $542 total
includes taxes & fees
May 13 - May 14
Norfolk Beach Cottage Rental
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 CA $217
CA $416 total
includes taxes & fees
May 13 - May 14
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
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 CA $231
CA $433 total
includes taxes & fees
May 13 - May 14
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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 CA $125
CA $160 total
includes taxes & fees
May 13 - May 14
Angie's Guest Cottage
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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

Lobby lounge
Wingate by Wyndham Chesapeake
2.5 star property
8.0 out of 10, Very good, (1007)
"The staff were very helpful and professional "
The price is CA $173
per night
May 13 - May 14
Wingate by Wyndham Chesapeake
Exterior
Fairfield Inn and Suites By Marriott Chesapeake
2.5 star property
8.8 out of 10, Excellent, (804)
"Nice clean place to rest my head for the night "
The price is CA $141
per night
May 28 - May 29
Fairfield Inn and Suites By Marriott Chesapeake
Seasonal outdoor pool
Delta Hotels by Marriott Virginia Beach Waterfront
4.0 star property
8.6 out of 10, Excellent, (961)
"This is probably one of the best hotels that we have ever stayed at. Staff was very kind and accommodating to our needs and let us know everything we needed to know about during our stay. The hotel itself was beautiful and very well kept. Sheets were clean along with the bathroom, balcony and suite entirely. Area around the hotel was very quiet for us and it’s nice to be away from the main point of VA Beach. We definitely will be back to visit again soon! "
The price is CA $217
per night
May 16 - May 17
Delta Hotels by Marriott Virginia Beach Waterfront
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 vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Jillian's Billiards, 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 Atrium Resort by VSA Resorts: This vacation home rental outside of Chesapeake is located by the ocean and has an indoor pool, an arcade game 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 vacation rentals are there in Chesapeake?

Expedia has 35 vacation 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 like Naval Station Norfolk and Sandbridge Beach.

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.