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Compare 1131 Vacation Homes in Chesapeake with updated reviews, rates, and availability.

Entire Home - Pet Friendly - Close to Beach - 2 Guests

10.0 out of 10, Exceptional, (99)
"We came into town to celebrate our grandsons birthdays and Christmas. We hosted our family for Christmas Eve dinner. Our hosts were very accommodating providing a table and table cloth. We couldn’t have had a more enjoyable time. We would highly recommend this home. "
Entire Home - Pet Friendly - Close to Beach - 2 Guests

Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

10.0 out of 10, Exceptional, (228)
"A fantastic location, near the beach and local family. Great entertaining space for a large dinner. Well stocked kitchen, great island! Loved the large table and open gathering space. Close to local store and the board walk. Would definitely rent again."
Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

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

9.0 out of 10, Wonderful, (20)
"The property was as described. Location worked well for us. Comfortable 4 nights in February. "
The price is SAR 518
SAR 1,379 total
includes taxes & fees
3 Mar - 4 Mar
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

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

9.6 out of 10, Exceptional, (63)
"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 SAR 416
SAR 913 total
includes taxes & fees
3 Mar - 4 Mar
The Art Door only minutes from beach

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

Inviting oceanfront home with amazing views, private pool & deck

8.4 out of 10, Very Good, (31)
"I booked the property to host a yoga retreat for 12 other women. The location was absolutely perfect. The property itself had a great layout for or needs-- including plenty of parking. We couldn't have asked for anything more. We'll certainly be back again!"
Inviting oceanfront home with amazing views, private pool & deck

Oceanfront home w/ocean views, WiFi, central AC, balcony, deck, washer/dryer

7.6 out of 10, Good, (19)
"Overall this property is nice. It is an older home with charm but also with general wear and age being by the ocean. The property could use a sprucing up and the kitchen ware is older. There is a musty smell but it is not over powering and expected with the age of the home and its location. My critical feedback is on the management side of our vacation. The company only offers one complimentary toilet paper roll, garbage bag, and paper towel roll, so if you plan to stay longer be prepared to buy...
Oceanfront home w/ocean views, WiFi, central AC, balcony, deck, washer/dryer

Trendy VIBE District Beachhouse - 4BR 3.5 Bath + Fast WIFI - W/D!

10.0 out of 10, Exceptional, (23)
"It was great had lots of room"
Trendy VIBE District Beachhouse - 4BR 3.5 Bath + Fast WIFI - W/D!

Oceanfront home w/private pool, beautiful views, WiFi, central AC, private W/D

8.8 out of 10, Excellent, (16)
"A lovely spot to unwind and relax. Very well equipped kitchen and a great layout."
Oceanfront home w/private pool, beautiful views, WiFi, central AC, private W/D

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.0 out of 10, Wonderful, (26)
"Stayed here with friends for a convention. Wonderful accommodations and a great place for us to all stay! We were close to downtown which was perfect for us. Would definitely stay here again! "
The price is SAR 484
SAR 1,305 total
includes taxes & fees
24 Feb - 25 Feb
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Recently Remodeled Northend Home Just Steps From Beach With Pool Table

9.6 out of 10, Exceptional, (138)
"Lovely property that needs some repairs and cleaning."
Recently Remodeled Northend Home Just Steps From Beach With Pool Table

4BD home with gameroom and pool, close to Langley & PTC!

9.6 out of 10, Exceptional, (13)
"The house was close to everything. It was spacious and well decorated. The keyless entry was convenient. We really enjoyed the games."
4BD home with gameroom and pool, close to Langley & PTC!

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

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!

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

10.0 out of 10, Exceptional, (143)
"Pinch me was perfecto to accommodate my friends and family. There was plenty of room for everyone to have their space and the teens were easily entertained, playing pool and foosball. The house had a fully equipped kitchen, which made entertaining easy. "
Breathtaking Ocean views at Pinch Me! 8bdrm, 6bath, private pool!

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

2.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect for our three families to spread out but also let the kids bunk up and enjoy downstairs all to themselves! We loved going down to the park, going to the market for donuts, walking the beach and enjoying the beautiful views. We can’t wait to stay here again next year. The house was well stocked, comfortable, and the host was very responsive to any questions.we loved it! "
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

9.2 out of 10, Wonderful, (85)
"Plenty of room and our group just LOVED staying here. Only a block or 2 from the beach, right over a cute walking bridge to the beach. I could have stayed for weeks. The host was my ideal host; responsive, understanding and has the best, detailed property manual to handle the house in any capacity. Definitely one of my favorite stays"
The price is SAR 825
SAR 2,569 total
includes taxes & fees
25 Feb - 26 Feb
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

Captain's Mansion 8bdrm/18guests vacation gem steps to beach

8.8 out of 10, Excellent, (3)
"The property was spacious and in a great location for our group of 14. The private beach was amazing! We rented both sides of the duplex, which was convenient as they share a backyard. One unit had a non-functioning refrigerator, but the owner responded promptly. After confirming it couldn't keep food cold, he replaced it the next day. Which required us to have to buy several bags of ice to keep food cold. Unfortunately, the dryer in the same unit also wasn't working and needed replacement,...
Captain's Mansion 8bdrm/18guests vacation gem steps to beach

Pool, hot tub, family friendly, walk to beach.

10.0 out of 10, Exceptional, (28)
"We needed a place for the whole family. This place was big enough for us to spread out. The kitchen was big enough that we didn't bump into each other and the big table held all of us easily. I would highly recommend this place especially in the summer when you can enjoy the swimming pool and the kayaks."
Pool, hot tub, family friendly, walk to beach.
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 property types in Chesapeake

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1290)
"Been here 3 times now and every time the staff is always helpful and just super nice. Overall just a really good team "
The price is SAR 273
SAR 537 total
includes taxes & fees
13 Mar - 14 Mar
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1437)
"Great place but need more bigger park spaces for guess"
The price is SAR 387
SAR 668 total
includes taxes & fees
23 Feb - 24 Feb
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

9.8 out of 10, Exceptional, (98)
"Our family of 4 enjoyed a quiet time in the outer banks at this lovely beach house. November isn't exactly the time most folks visit the beach, but we've spent most of our lives in the far north, so the "chilly weather" didn't prevent us from enjoying kayaking in the inner channels and viewing the sunset from the crow's nest. We found the kitchen very adequate; we were able to cook a lovely thanksgiving dinner and ate quite well the entire time. We packed all our needs/food for the weekend so...
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
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.