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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Chesapeake

Sunsets | Beach + Pool + Pickleball | Pet Friendly
Terrace/patio

Sunsets | Beach + Pool + Pickleball | Pet Friendly

9.8 out of 10, Exceptional, (22)
"The house and owners were amazing - we had an incredible time and will absolutely be visiting again."
Sunsets | Beach + Pool + Pickleball | Pet Friendly
Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided
Smart TV, books, video library, stereo

Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided

10.0 out of 10, Exceptional, (192)
"Our stay here was excellent! We enjoyed using the kayaks, trying a little fishing, and having a bonfire. The location of the cottage was perfect for spending the day on beach and then coming back to relax in the evening."
Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Beach nearby

Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

8.0 out of 10, Very good, (4)
"The location is great for a family with pets. The check in and out process was simple and the host was responsive. No complaints! "
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
6 Block to oceanfront and in the center of the vibe district!
Fridge, microwave, oven, stovetop

6 Block to oceanfront and in the center of the vibe district!

9.0 out of 10, Wonderful, (40)
"Perfect home as advertised! Perfect location. Would recommend and would stay again. "
6 Block to oceanfront and in the center of the vibe district!
Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning
Beach nearby

Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning

7.8 out of 10, Good, (6)
"Our stay was nice. The house was clean."
Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning
Pink Flamingo at the Beach
Property grounds

Pink Flamingo at the Beach

8.6 out of 10, Excellent, (16)
"older place but very nice and close to the beach"
Pink Flamingo at the Beach
Salt Heir: North End vintage beach cottage only 1 block to beach & park!
Property grounds

Salt Heir: North End vintage beach cottage only 1 block to beach & park!

10.0 out of 10, Exceptional, (12)
"This is a perfect cottage in VA Beach. The golf cart was a huge plus!"
Salt Heir: North End vintage beach cottage only 1 block to beach & park!
Cozy Suite at the Beach
On the beach, sun-loungers

Cozy Suite at the Beach

8.4 out of 10, Very good, (60)
"It was alright "
Cozy Suite at the Beach
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

9.0 out of 10, Wonderful, (100)
"If you’re looking for a place for you to have a safe space with your family, young or old, with all the amenities that you would want from your own home this is it. If you’re a veteran, there’s multitude of bases nearby with commissary’s to get groceries for the week to help the budget. "
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Treetop Rustic Beach Front 2 Bedroom Apartment
Exterior

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (25)
"Repeat guest.. stayed in another unit previously *loft property.Property is very close to the beach, can walk into the sand from the property. Pet friendly is a plus.. lots of doggos on the beach.Property has the basics.. minimal items in unit, so you need to bring quite a bit of things to make your trip complete. Owners have several units, so amenities are shared. Husband and I used the charcoal grill and set by the firepit in the sand. Not sure id stay in this particular unit again, but id...
Treetop Rustic Beach Front 2 Bedroom Apartment
Sandy Dunes BeachFront Cottage - Beach Front
On the beach

Sandy Dunes BeachFront Cottage - Beach Front

8.0 out of 10, Very good, (29)
"The outside of the property needs some upkeep but we didn’t mind because it was such a charming place."
Sandy Dunes BeachFront Cottage - Beach Front
Cozy Mother-in-Law Suite
Iron/ironing board, free WiFi, bed sheets

Cozy Mother-in-Law Suite

8.8 out of 10, Excellent, (89)
"Small unit to the rear of rental property. Could not stay in property for length of planned trip."
Cozy Mother-in-Law Suite
Cozy Bay Cottage private backyard blocks from beach!
Dining

Cozy Bay Cottage private backyard blocks from beach!

9.0 out of 10, Wonderful, (37)
"Clean and up-to-date home. Close to the beach. Convenient and comfortable. Would rent again. "
The price is NZ$724
includes taxes & fees
31 Aug - 1 Sept
Cozy Bay Cottage private backyard blocks from beach!
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private
On the beach

Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

8.6 out of 10, Excellent, (14)
"Owner contacted us on day of scheduled arrival and told us property was unavailable due to sewage issue. Stuff happens I get it. Odd that they tried to provide us with two lesser properties, one with one less bedroom and the other not on the beach. They refused to lower . "
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private
Secluded, stunning 🌊water views 1 mi from beach🏝️☀️
Smart TV, offices

Secluded, stunning 🌊water views 1 mi from beach🏝️☀️

9.6 out of 10, Exceptional, (62)
"A beautiful home to enjoy the sunshine and Dawn was a wonderful host!"
Secluded, stunning 🌊water views 1 mi from beach🏝️☀️
OBX 4X4 Ocean View- Pipers Place Wild Horse Haven!!!
Interior

OBX 4X4 Ocean View- Pipers Place Wild Horse Haven!!!

9.6 out of 10, Exceptional, (5)
"Be prepared for a 10 mile drive on the beach! Would definitely stay in this area again."
OBX 4X4 Ocean View- Pipers Place Wild Horse Haven!!!
Shore Relaxing ocean views and wild horses Farm house cottage dog friendly
Beach nearby, sun-loungers

Shore Relaxing ocean views and wild horses Farm house cottage dog friendly

10.0 out of 10, Exceptional, (98)
"Had a great time - house was wonderful!"
Shore Relaxing ocean views and wild horses Farm house cottage dog friendly
Adorable Chesapeake Bay Beach Cottage B Just 1 Block from the Sand!
Fridge, microwave, oven, stovetop

Adorable Chesapeake Bay Beach Cottage B Just 1 Block from the Sand!

9.4 out of 10, Exceptional, (16)
"Very clean and great access to the beach and many restaurants. The only negative is a very busy street but once you get used to that it isn't bad."
Adorable Chesapeake Bay Beach Cottage B Just 1 Block from the Sand!
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi
On the beach

Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

8.8 out of 10, Excellent, (47)
"Had an overall nice stay. Very clean. Great location was able to take a walk on the beach and that was definitely needed. Was in town due to family emergency and booked quickly. In the pictures there are 3 beds in room but there were only 2 when we got there a full size and twin. So my daughters were mad they had to sleep together but they got over it. Living room was cold and bedroom got hot.We also booked for 5 people but there were only 3 towels and 3 wash cloths. But made the best of it and...
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi
Deluxe Waterview Cabin in Amenity-Filled Currituck Sound Campground (WV89)
TV

Deluxe Waterview Cabin in Amenity-Filled Currituck Sound Campground (WV89)

9.4 out of 10, Exceptional, (17)
"It was a very nice place and location"
Deluxe Waterview Cabin in Amenity-Filled Currituck Sound Campground (WV89)
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

DoubleTree by Hilton Virginia Beach

DoubleTree by Hilton Virginia Beach

10/10 Excellent
"Great "
Jarmy 2-night trip
Posted 7 hours ago
DoubleTree by Hilton Virginia Beach

Frequently asked questions

What is there to do in Chesapeake near my cottage?
Chesapeake has enough activities and sights to keep you amused for weeks (or months!), beginning with Chesapeake Golf Club. Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Square Mall are other well-known attractions. If you have time to spare, Greenbrier Mall and Chesapeake Veterans' Memorial are nice finishing touches to your itinerary.