A golf course, a large building complex, and a marina by a river.

Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesapeake vacation homes

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is CA $197
CA $863 total
includes taxes & fees
Nov 9 - Nov 10
Entire Home in Chesapeake, Virginia
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

2. 3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is CA $216
CA $415 total
includes taxes & fees
Nov 4 - Nov 5
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

3. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is CA $112
CA $373 total
includes taxes & fees
Nov 1 - Nov 2
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

4. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (32 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is CA $151
CA $420 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

5. Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (49 reviews)
"The location suited our business travel needs. Never received checkin details so had to call. WiFi did not work and no response to multiple inquiries about the issue. Areas of damage throughout the house."
United States
Jebediah
The price is CA $181
CA $491 total
includes taxes & fees
Oct 28 - Oct 29
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a window with a view.

6. Spacious Portsmouth Getaway w/Game Room

Spacious Portsmouth Getaway w/Game Room
Portsmouth
8.0 out of 10, Very good, (3 reviews)
"This house was the perfect fit for our weekend getaway. My husband was a volunteer at Farm Aid and my son and I brought the dog and had a nice little weekend. It was clean and just as the host described. All the amenities were there. We would stay again if we were in the area."
United States
Susan L.
The price is CA $189
CA $557 total
includes taxes & fees
Oct 28 - Oct 29
Spacious Portsmouth Getaway w/Game Room
A poolside area with a covered seating area, a pool, and a white fence.

7. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.8 out of 10, Excellent, (13 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is CA $200
CA $340 total
includes taxes & fees
Nov 4 - Nov 5
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A modern living room with a fireplace, a kitchen in the background, and a dining area with bar stools.

8. Quiet & Private, Comfy Beds, Fire Pit, & Bikes

Quiet & Private, Comfy Beds, Fire Pit, & Bikes
Portsmouth
8.4 out of 10, Very good, (6 reviews)
"Home was perfect for my husband and I and our adult daughter and plenty of room when our other daughter and husband visited. We had enough room to eat and play games. Great yard for dogs to run, sniff and play! Beds were comfy. "
United States
Marybeth T.
The price is CA $203
CA $576 total
includes taxes & fees
Oct 28 - Oct 29
Quiet & Private, Comfy Beds, Fire Pit, & Bikes
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

9. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is CA $364
CA $869 total
includes taxes & fees
Oct 28 - Oct 29
Wooded Wonderland
A living room with a flat-screen TV mounted on the wall, a brown leather sofa with patterned cushions, a patterned rug, and a dining area in the background.

10. ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!

ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!
Norfolk
10.0 out of 10, Exceptional, (1 review)
"Great stay"
United States
Anonymous traveller
The price is CA $226
CA $433 total
includes taxes & fees
Nov 2 - Nov 3
ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!
A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

11. 3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake
Portsmouth
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Quiet neighborhood with a beautiful lake view."
United States
Muun Queen M.
The price is CA $239
CA $623 total
includes taxes & fees
Oct 28 - Oct 29
3D Theater plus Dock on Small Lake
A beach with a pier extending into the water, featuring a building labeled 'BART & GRILL'.

12. Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Norfolk
8.8 out of 10, Excellent, (92 reviews)
"Nice small rustic cottage right on the beach. Enjoyed my time there."
United States
Mary W.
The price is CA $200
CA $392 total
includes taxes & fees
Nov 8 - Nov 9
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

13. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (14 reviews)
"The property is spacious and conveniently located near the beach and restaurants. It is family-friendly and the host is exceptionally communicative. I plan to return in the future."
United States
Sheryll
The price is CA $141
CA $472 total
includes taxes & fees
Oct 28 - Oct 29
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

14. Charming 3bd - Near beaches - Foosball & Backyard

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.8 out of 10, Exceptional, (16 reviews)
"The property was great, 5 min walk to the beach. House was bright and cheery with plenty of space for our stay."
United States
Debbie M.
Charming 3bd - Near beaches - Foosball & Backyard
A kitchen with wooden cabinets, a refrigerator, a microwave, a stove, and a ceiling fan.

15. Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Norfolk
8.4 out of 10, Very good, (28 reviews)
"Great host and great property! Will be coming back in the future! Loved the fire pit feet from the beach!!"
United States
Benjamin C.
The price is CA $226
CA $434 total
includes taxes & fees
Oct 29 - Oct 30
Beachfront Bungalow w/ BEST Location in Ocean View!
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

16. Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
8.6 out of 10, Excellent, (10 reviews)
"Very Clean, beautiful property situated just blocks from the beach. Neighborhood was very friendly. The entire stay in this charming cottage was delightful!"
United States
Todd C.
The price is CA $189
CA $524 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

17. Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.6 out of 10, Exceptional, (23 reviews)
"The property was conveniently located at the beach yet close to Regent University. A great parents’ weekend and graduation getaway spot."
United States
Thomas M.
The price is CA $189
CA $608 total
includes taxes & fees
Nov 2 - Nov 3
Beach Bungalow King Bed 1 Floor Living
A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

18. Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.2 out of 10, Wonderful, (7 reviews)
"Very nice place. We enjoyed the fire pit every night and the easy walk to the beach was a plus."
United States
Robin T.
The price is CA $230
CA $663 total
includes taxes & fees
Nov 22 - Nov 23
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A view through a window with a grid pattern, overlooking a calm sea and a sandy beach with a small structure and a lifebuoy.

19. Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.8 out of 10, Exceptional, (32 reviews)
"Great location. Excellent view. The F22 Raptors were cool to see. Not so loud. Host was great. The place does not have a full size oven, so plan accordingly. Beds were comfy."
United States
Jim G.
The price is CA $175
CA $645 total
includes taxes & fees
Oct 28 - Oct 29
Sojourn Aviators Dream on Back River
A room with a dining table and chairs, a door, a radiator, and a refrigerator.

20. Cozy 1-bedroom barn in marvelous Hampton with AC

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
10.0 out of 10, Exceptional, (2 reviews)
"It was a nice place. It was like a nice studio sized ap with a lower level living room. Very close to the university where I was at the entire weekend. The owner is nice and easy to talk to."
United States
Nicole C.
The price is CA $141
CA $536 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 1-bedroom barn in marvelous Hampton 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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

8/10 Good
"Beach hotels in high tourist areas are usually unpredictable especially when booking for a first time. We were pleasantly surprised by our experience here. The hotel is older, and the parking garage part of the building definitely showed its age, however the hotel was well maintained, and clean. The oceanfront rooms were kept updated and clean. The beds were comfortable. The view was beautiful! A nice breakfast, with great seating area were included. And the price was more reasonable than so many in the area. Grounds were kept updated. So many great ammenities. And every staff member greeted us with a smile, and hello. We would definitely stay here again. Thank you for such a comfortable stay."
Derrick 2-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
291
Accommodation
1258 Vacation Homes
Lowest Price
CA $340
Highest Price
CA $869

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