Holiday Homes in Chesapeake

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Featured Holiday Homes in Chesapeake and around

The Atrium Resort, Virginia Beach by Vacatia
Beach nearby
The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
8.2 out of 10, Very good, (1292)
"Great stay at a great price."
The Atrium Resort, Virginia Beach by Vacatia
The Art Door only minutes from beach
Property grounds
The Art Door only minutes from beach
9.8 out of 10, Exceptional, (59)
"This was a perfect little space for us for 2 days."
The price is €239
includes taxes & fees
3 Dec - 4 Dec
The Art Door only minutes from beach
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Terrace/patio
3-bedroom home away from home in fabulous Chesapeake, Virginia.
2.0 star property
10.0 out of 10, Exceptional, (13)
"We stayed three nights and couldn't have asked for a better experience. Check in was easy and the location was in a very nice neighborhood. His directions made it easy to find. We felt at home from the time we walked in. The home was very clean and had every amenity we needed. The beds were nice and comfortable. Our pup enjoyed the big back yard. It was a pleasure to rent from Eric, he responded very quickly if we needed anything. There is not one negative we can say. Would definitely...
The price is €325
includes taxes & fees
4 Dec - 5 Dec
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
Fridge, microwave, oven, stovetop
Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
10.0 out of 10, Exceptional, (219)
"Myself, my husband, my 5 year old, 1 year old, & 5 year old Aussiedoodle all had a wonderful stay. The details in this home were so well thought out. We enjoyed being in walking distance of our favorite coffee roaster Fathom, a short walk from the beach, & lots of other fun places. The neighborhood overall is really quiet. At times you hear the nearby school but otherwise the neighborhood has a very welcoming atmosphere! We cooked a couple of meals in the kitchen, & ran a couple loads of...
Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Fridge, microwave, oven, stovetop
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
9.4 out of 10, Exceptional, (92)
"House served us fairly well for a 5 night family get together. Ages 2 to 75. Guests from four different states. Several commented their beds were better than home. We enjoyed the huge dining room table, close proximity to the beach, the air show at NAS Oceana and the iFly experience nearby. Unfortunately, when we arrived at the home it was pretty warm inside. We set all the thermostats to 72 degrees and waited several hours for the house to cool down but only the 3rd floor and half of the 2nd...
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Oceanfront home w/elevator, private outdoor pool & hot tub - wedding-friendly
Terrace/patio
Oceanfront home w/elevator, private outdoor pool & hot tub - wedding-friendly
8.2 out of 10, Very good, (15)
"Great beach, house has nice layout for big family, nice furniture, pool, hot tub... Needs upgrades to cookware, uneven temperature depending on room, floor mats at entries new mattress room 3...regardless we made some really great memories here that 11 kids will never forget! "
Oceanfront home w/elevator, private outdoor pool & hot tub - wedding-friendly
NEW! Residential Retreat. Located minutes to the Oceanview beach and Naval base.
Smart TV
NEW! Residential Retreat. Located minutes to the Oceanview beach and Naval base.
9.6 out of 10, Exceptional, (39)
"The home was comforted and roomy which allowed for family time and a little quiet time alone. The home is simple and clean "
NEW! Residential Retreat. Located minutes to the Oceanview beach and Naval base.
A block to the beach!
Terrace/patio
A block to the beach!
9.6 out of 10, Exceptional, (55)
"The house was cute, clean and easy walking distance to the beach. "
A block to the beach!
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Outdoor dining
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
9.6 out of 10, Exceptional, (92)
"Myself, my husband and my son really enjoyed our stay. Very nice and quiet area for rest and relaxation. Beautiful walk to the beach along the canopy of trees walkway. Right next to the military base so felt very safe as well. Wish there was more availability for future visits but property appears booked for the next 2 years."
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Farmhouse Beach Home 2 Bdrm 2 blocks from beach!
Beach nearby
Farmhouse Beach Home 2 Bdrm 2 blocks from beach!
10.0 out of 10, Exceptional, (88)
"Cat and Chris provided a peaceful, quiet and very clean respite for a Virginia Beach getaway. Their guidebook is very well done, detailing recommended activities, restaurants and helpful hints. The location at the end of the street was perfect. If we return to the area, we will hope to stay again! Thank you. "
Farmhouse Beach Home 2 Bdrm 2 blocks from beach!
Tiny House Near Beach & Naval Base - Privacy Fence
Beach
Tiny House Near Beach & Naval Base - Privacy Fence
9.8 out of 10, Exceptional, (21)
"We had a few hiccups during our stay but they were address quickly and Esmel worked with us to resolve them. The house is super cute and perfect for a short stay. Everything was a short drive away so it was nice being close to everything without being right in the middle of town"
Tiny House Near Beach & Naval Base - Privacy Fence
Semi-Oceanfront , Views! 5 BR Pet Friendly, Pool, Hot Tub, Location!
Outdoor pool
Semi-Oceanfront , Views! 5 BR Pet Friendly, Pool, Hot Tub, Location!
9.0 out of 10, Wonderful, (131)
"The house is right next to the beach. Internet went down but the host had it fixed during our stay. Pool and hot tub was nice. Plenty of space."
Semi-Oceanfront , Views! 5 BR Pet Friendly, Pool, Hot Tub, Location!
Serenity on the Bay-Complimentary Sunrise & Sunset Views
4 bedrooms, WiFi, bed sheets
Serenity on the Bay-Complimentary Sunrise & Sunset Views
9.4 out of 10, Exceptional, (21)
"This house was a nice stay for our family. Plenty of room to spread out and beautiful view. Host was great at communicating. Would definitely consider staying here again!"
Serenity on the Bay-Complimentary Sunrise & Sunset Views
Hilton Village Home
Property grounds
Hilton Village Home
9.6 out of 10, Exceptional, (28)
"This place was so great to stay at!"
The price is €288
includes taxes & fees
23 Nov - 24 Nov
Hilton Village Home
Silver Strand-Renovated 2022, Sandbridge/Bayfront
Interior
Silver Strand-Renovated 2022, Sandbridge/Bayfront
9.8 out of 10, Exceptional, (40)
"Our stay was great for all five of us. We had plenty of room to spread out but the space still felt connected. We enjoyed the pool and other common areas. Nice experience! "
Silver Strand-Renovated 2022, Sandbridge/Bayfront
Adorable Beach bungalow a BLOCK from the Beach
Property grounds
Adorable Beach bungalow a BLOCK from the Beach
7.6 out of 10, Good, (4)
"Ver"
The price is €349
includes taxes & fees
23 Nov - 24 Nov
Adorable Beach bungalow a BLOCK from the Beach
Brand New Buckroe Beach 2 Bedroom, sleeps 5! Walk to the Beach!
Fridge, microwave, oven, stovetop
Brand New Buckroe Beach 2 Bedroom, sleeps 5! Walk to the Beach!
9.6 out of 10, Exceptional, (20)
"We loved our stay at this property. It was super close to the beach and great restaurants. It was quiet and the amenities were plenty. It’s a perfect home away from home as I visit my son who we were dropping off for his freshman year during this day."
Brand New Buckroe Beach 2 Bedroom, sleeps 5! Walk to the Beach!
Historic Old Towne Southern Charm
2 bedrooms, desk, iron/ironing board, free WiFi
Historic Old Towne Southern Charm
9.8 out of 10, Exceptional, (12)
"Latonya was a great host. She greeted us when we arrived at the Property and provided some dinner recommendations. The home was clean and inviting which was perfect for a short stay. We would definitely book again. "
Historic Old Towne Southern Charm
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
On the beach
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
7.0 out of 10, Good, (2)
"Our stay was okay. The house was in an excellent location to the beach, however very difficult to find from the road. The house was a great size & the beds were so comfortable. I rate this with a 3 because I felt like there were several things that desperately need updated. The faucets in the bathroom were heavily rusted and leaking. When taking a shower, our faucet diverter broke so we werent able to take a shower the last day of our stay. There is not much of an ocean view as there is a lot of...
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning
Cozy Ocean Side Beach Cottage at Fantastic Location North End of Virginia Beach
Dining
Cozy Ocean Side Beach Cottage at Fantastic Location North End of Virginia Beach
9.8 out of 10, Exceptional, (74)
"Great stay."
Cozy Ocean Side Beach Cottage at Fantastic Location North End of Virginia 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

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Exterior
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
3.0 star property
8.0 out of 10, Very good, (1403)
"Everything was excellent from the time I checked in great help from kat who check me in to my stay every thing was top rated thank again for everything "
The price is €137
includes taxes & fees
5 Dec - 6 Dec
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Ocean Key Resort by VSA Resorts
Indoor pool
The Ocean Key Resort by VSA Resorts
3.0 star property
7.8 out of 10, Good, (1270)
"Stayed for 1night room was nice and very clean friendly quiet. "
The price is €122
includes taxes & fees
5 Dec - 6 Dec
The Ocean Key Resort by VSA Resorts
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby
The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
8.2 out of 10, Very good, (1292)
"Great stay at a great price."
The Atrium Resort, Virginia Beach by Vacatia
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.