Holiday Homes in Chesapeake

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Featured Holiday Homes in Chesapeake and around

Charming Tiny Cottage

10.0 out of 10, Exceptional, (33)
"Quiet area, great proximity to beach. Can hear waves and watch sunrise on front deck while sipping coffee. Wild horses walk through yard. "
Charming Tiny Cottage

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

9.0 out of 10, Wonderful, (65)
"Like the fire pit outside and so close to the beach and the pier the only downside is 1 bedroom doesn’t have AC but other than that it’s perfect We’ll stay there again "
The price is €394
includes taxes & fees
22 Jul - 23 Jul
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!

9.6 out of 10, Exceptional, (165)
"Great location. Listing was accurate. "
A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!

Sweet home to share with the family

8.8 out of 10, Excellent, (28)
"I stayed here for my birthday to hang out with friends and we loved it. The host was super sweet and very accommodating. Even let us stay later and check in early."
The price is €529
includes taxes & fees
21 Jul - 22 Jul
Sweet home to share with the family

Your own private beach with this charming 3-bedroom beachfront house!

9.6 out of 10, Exceptional, (15)
"We enjoyed 4 days and 3 nights at this cute home. The house was just perfect for our family and we throughly enjoyed the porch and back yard which is where we spent most of our time. The house had everything we needed and more. The walk down to the beach was beautiful and it felt like we had our own private beach. If you are looking to get away from the hustle and bustle this is a great place. Neighbors are close in proximity, but we never really saw anyone and it was all quiet. We did meet one...
Your own private beach with this charming 3-bedroom beachfront house!

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (83)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is €218
includes taxes & fees
14 Aug - 15 Aug
The Art Door only minutes from beach

Tiny House Near Beach & Naval Base - Privacy Fence

9.8 out of 10, Exceptional, (25)
"Great little place! Clean, safe, & has everything you need for a weekend getaway! "
Tiny House Near Beach & Naval Base - Privacy Fence

☆ Beachfront Home w/ Stunning Views, Hot Tub, Luxury Kitchen & Private Beach!

10.0 out of 10, Exceptional, (40)
"The owner is easily accessible and they maintain a fantastic property true to its listing. My teenagers loved the property and our stay."
☆ Beachfront Home w/ Stunning Views, Hot Tub, Luxury Kitchen & Private Beach!

Coastal Luxury Canal Retreat • Luxury Amenities • Pool • Hot Tub • Walk to Beach

10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed 3-day Independence Day holiday on Sandbridge Beach. The check-in process was effortless and Roger was very prompt in answering questions before and throughout our stay. We really loved this home because it offered so much of what we wanted to do on vacation including a large swimming pool, hot tub, and boat/kayak access on the canal. The beach was a short walk out of the neighborhood and across the street to the quiet Sandbridge Beach. We liked the home and location so...
Coastal Luxury Canal Retreat • Luxury Amenities • Pool • Hot Tub • Walk to Beach

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

8.8 out of 10, Excellent, (58)
"Great stay "
The price is €428
includes taxes & fees
27 Jul - 28 Jul
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

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

9.8 out of 10, Exceptional, (103)
"Property was perfect for a small family trip to the beach. Just a short walk to a beautiful beach. House was clean and well appointed"
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

Beach Cottage a short walk from the waves!

9.2 out of 10, Wonderful, (23)
"Me and my family had a wonderful time staying here on Carova Beach. This place was clean and ready to go for visitors and had everything needed to enjoy a nice secluded stay on the beach! Thanks!"
Beach Cottage a short walk from the waves!

Coastal Sea.Rinity🌊

7.8 out of 10, Good, (16)
"Was a cute place to stay for a weekend. My girlfriends and I enjoyed our time. It was so close to the beach! Some things were a little rundown or broken but overall was a very nice stay. Host is very nice and had great communication!"
Coastal Sea.Rinity🌊

Charming 4-bedroom house with WiFi and AC in fabulous Norfolk

2.0 star property
9.4 out of 10, Exceptional, (3)
"Convenient to beach for one night in town"
The price is €409
includes taxes & fees
13 Aug - 14 Aug
Charming 4-bedroom house with WiFi and AC in fabulous Norfolk

Cozy Currituck Home w/ Fire Pit near Ferry!

9.8 out of 10, Exceptional, (26)
"Our recent stay was great. The property was exactly as described—clean and comfortable, everything we needed for a relaxing getaway. The location was perfect."
Cozy Currituck Home w/ Fire Pit near Ferry!

Cozy & Clean Norfolk Cottage- Fenced Yard for Dogs

10.0 out of 10, Exceptional, (23)
"Great location, clean & everything we needed was here. We would definately come back"
Cozy & Clean Norfolk Cottage- Fenced Yard for Dogs

Oceanside, Wild Horses! Beach getaway, remote location, 4x1701, Sandy Paws Retreat

Oceanside, Wild Horses! Beach getaway, remote location, 4x1701, Sandy Paws Retreat

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

9.8 out of 10, Exceptional, (175)
"This property is well maintained and is just as promised in the description. Owner is very helpful and responsive."
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

4.0 star property
7.4 out of 10, Good, (41)
"First want to start off by saying the house is as described actually better then the photos online led us to believe. It's an older house but was clean and decorated beautifully. For the money, description, and space you get staying in this home I would definatley recomend you staying here. It's not a 5 star luxury resort, but I gave 5 stars for the house being it was better then what we expected. Our family enjoyed our stay."
The price is €432
includes taxes & fees
3 Aug - 4 Aug
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

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

9.4 out of 10, Exceptional, (92)
"Great spot with lots of room. Beautiful neighborhood. Easy walk to the beach. Great amenities!"
The price is €1,194
includes taxes & fees
24 Jul - 25 Jul
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan 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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Top Chesapeake Hotel Reviews