Holiday Homes in Chesapeake

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Our top choices for Chesapeake holiday homes

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, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
3-bedroom home away from home in fabulous Chesapeake, Virginia.

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (104 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is €196
includes taxes & fees
3 Feb - 4 Feb
The Art Door Duplex only minutes from beach

Comfort near the water and University

Comfort near the water and University
Elizabeth city
7.6 out of 10, Good, (5 reviews)
"We had a nice stay. Thank you. "
United States
Rebecca S.
The price is €236
includes taxes & fees
3 Feb - 4 Feb
Comfort near the water and University

Mermaids & Mutts 3 Bedroom Bungalow by RedAwning

Mermaids & Mutts 3 Bedroom Bungalow by RedAwning
3.0 star property
Cottage Line
Mermaids & Mutts 3 Bedroom Bungalow by RedAwning

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, (25 reviews)
"The place was noce and quiet. "
United States
Tomar B.
The price is €249
includes taxes & fees
3 Feb - 4 Feb
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Willoughby Spit
9.0 out of 10, Wonderful, (71 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is €214
includes taxes & fees
5 Mar - 6 Mar
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Water Front Delight on the Bay

Water Front Delight on the Bay
Willoughby Spit
7.8 out of 10, Good, (25 reviews)
"Everything was very nice really enjoyed "
United States
Deborah B.
The price is €287
includes taxes & fees
28 Feb - 1 Mar
Water Front Delight on the Bay

Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.8 out of 10, Exceptional, (15 reviews)
"This was a beautiful property. Plenty of room for Family Fun and very close to the beach. The host was very helpful and communicated with us about the property. I would definitely stay here again. "
United States
Tamika H.
The price is €344
includes taxes & fees
3 Feb - 4 Feb
Beach Bungalow King Bed 1 Floor Living

Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.6 out of 10, Exceptional, (29 reviews)
"My family enjoyed the experience of staying near the water. The views were lovely! "
United States
Precious E.
The price is €384
includes taxes & fees
3 Feb - 4 Feb
Sojourn Aviators Dream on Back River

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is €289
includes taxes & fees
3 Feb - 4 Feb
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

#Buckroe Bungalow ~Escape to the Beach 2mins Away!

#Buckroe Bungalow ~Escape to the Beach 2mins Away!
Hampton
9.0 out of 10, Wonderful, (18 reviews)
"Enjoyed our staycation .Will be back."
United States
Josie B.
The price is €258
includes taxes & fees
3 Feb - 4 Feb
#Buckroe Bungalow ~Escape to the Beach 2mins Away!

Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is €225
includes taxes & fees
5 Feb - 6 Feb
Large 2 bedroom | Queen beds | Safe Area

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is €359
includes taxes & fees
4 Mar - 5 Mar
Sojourn | Coastal Cottage | 3 BR

Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (46 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is €279
includes taxes & fees
16 Feb - 17 Feb
Cozy Beach Home in Oceanview

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.2 out of 10, Wonderful, (27 reviews)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
4 Bedroom Cottage - 5 Minutes from both beaches

Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.

Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.
Corolla
9.8 out of 10, Exceptional, (16 reviews)
"Aaron and Kim were fabulous! From personal escorts at high tide to trips bringing a grill and charcoal. All members of my party were beyond impressed "
United States
Jacquie M.
The price is €753
includes taxes & fees
4 Feb - 5 Feb
Octopus Oasis Carova Beach OBX WILD HORSES. 4x4/AWD is needed to access house.

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
9.6 out of 10, Exceptional, (4 reviews)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is €192
includes taxes & fees
3 Feb - 4 Feb
Knot Three- Balcony View of ICW- Dog Friendly!

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
8.6 out of 10, Excellent, (7 reviews)
"Cute little bungalow on the beach. Beautiful sunrises. Location is great. Very clean. Has everything you need!!! The pier is a 2 min walk. "
United States
Virginia T.
The price is €226
includes taxes & fees
3 Feb - 4 Feb
Beachfront Bungalow w/ BEST Location in Ocean View!

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

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.6 out of 10, Exceptional, (5 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.
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

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
8.0 out of 10, Very good, (1 review)
"Host is communicative and relaxed (not trying to micromanage your stay). I forgot to check the pics and descriptions for a microwave but there isn’t one. Alternatively, there is a hot plate and a pot. I gave 4 out of 5 stars due to the coffeemaker not working and having one washcloth for two people but it was pleasant other than that. "
United States
Courtney R.
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
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

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Chesapeake Holiday Homes information

Number of reviews
482
Accommodation
1390 Holiday Homes
Lowest Price
€192
Highest Price
€753