Holiday Rentals in Chesapeake
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45 rentals in Chesapeake.
King Guest Suite - A TOGAR Vacation Rental
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Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
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Private, Spacious Studio Apartment, Bathroom
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Studio | Free Breakfast. Indoor Pool & Hot Tub
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Studio | Free Breakfast. Indoor Pool & Hot Tub.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Great Studio | Pool & Hot Tub. Your Next Vacation
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Rural Tiny House in the Edge Of the Woods
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
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Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business
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King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach
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Large 1-Bedroom private room w/movie theater & free parking.
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The Sparks Home! Relaxing Space + Lux Kitchen
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NEWLY REMODELED 2 BEDROOM DUPLEX
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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FRESHLY RENOVATED 2 BEDROOM DUPLEX
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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GreenCharm - King Suite, 3BR, 4TVs- 30Day discount
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
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HY - King Suite, 4Tvs, Wi-Fi, 3BR, 30 day discount
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The Full House
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Comfortable Home | Long Stay Discount Available
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Camelot, 3B 2BA, corner lot home in culdesac
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely space while away from home. 19 miles from beach
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Welcome to our cozy home in Chesapeake
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Country Escape Home in the Woods- Chesapeake, VA
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Fully renovated and Modernized home in Chesapeake
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Very Decent 4 bedroom / 2 full bath. Located within the heart of the City.
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King Bed Colonial Cape Cod - Rest & Relaxation!
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Beautifully appointed, spacious ranch style home located in Greenbrier!
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Ultimate Vacation Home
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Beautiful custom built home in the country
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business
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3-bedroom home away from home in fabulous Chesapeake, Virginia.
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Cosy studio apartment over garage. Half hour from VB - 1 hour from Outerbanks
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Southern Charm Warm and Welcome Entire home hosted by Annette 4 guests
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy 3-bedroom house in lovely Chesapeake with WiFi, AC
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy 2-bedroom condo with WiFi and AC in enchanting Chesapeake
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Spacious 5-bedroom house with AC, WiFi in delightful Chesapeake
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historical section of Chesapeake. Propertie nice and groomed quiet neighborhood.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Farm Cottage: The Cutest Retreat – 3-Bedroom Chesapeake Cottage with WiFi & AC!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spacious home in Chesapeake
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil Paradise Nature Sanctuary. Pool, red barns and horses, goats and more.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful home in Chesapeake
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Townhome Newly renovated in GreatBridge, Chesapeake, ⭐️⭐️⭐️⭐️⭐️ on another site
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10 Mi to Norfolk: Chesapeake Haven w/ Yard!
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Showing results 1-45 of 45
Frequently Asked Questions about Chesapeake
- Yes, here are some popular holiday rentals in Chesapeake that have a pool:
- King Guest Suite - A TOGAR Vacation Rental
- Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
- Private, Spacious Studio Apartment, Bathroom
- Yes, here are some popular holiday rentals in Chesapeake that have internet access:
- King Guest Suite - A TOGAR Vacation Rental
- Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
- Private, Spacious Studio Apartment, Bathroom
- The best pet friendly rentals in Chesapeake are:
- King Guest Suite - A TOGAR Vacation Rental
- Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
- The Full House
- Some of the most popular kid friendly rentals in Chesapeake are:
- King Guest Suite - A TOGAR Vacation Rental
- Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
- Private, Spacious Studio Apartment, Bathroom
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