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Holiday homes in Chesapeake

Enjoy your stay and find the best Holiday homes in Chesapeake at affordable prices

Searching for a holiday home in Chesapeake (Virginia)? Explore a great selection of vacation homes in Chesapeake to find the one that best fits to your needs, starting from $117 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Chesapeake and region (30 miles)
The Lucas Cheery House with Fenced Backyard! in Chesapeake, USA

The Lucas Cheery House with Fenced Backy...

Holiday home in Chesapeake, Virginia
The Lucas Cheery House with Fenced Backyard! is located in Chesapeake, 23 km from Virginia Beach National Golf Club, 24 km from Mount Trashmore Park, ...
  • Parking
  • Fitness centre

no reviews

from $142.00 Show details »

The Sparks Home! Relaxing Space + Lux Kitchen in Chesapeake, USA

The Sparks Home! Relaxing Space + Lux Ki...

Holiday home in Chesapeake, Virginia , 765 Big Bear Lane
Located 33 km from Mount Trashmore Park, 34 km from Virginia Beach National Golf Club and 40 km from Naval Air Station Oceana, The Sparks Home!
  • Parking
  • Family rooms

no reviews

from $202.50 Show details »

Virginia Beach Home Sleeps 8 Game Rm and Meditation Rm in Virginia Beach, USA

Virginia Beach Home Sleeps 8 Game Rm and...

Holiday home in Virginia Beach near Chesapeake, Virginia , 125 Bangor Avenue
Boasting garden views, Virginia Beach Home Sleeps 8 Game Rm and Meditation Rm offers accommodation with a garden and a patio, around 7.7 km from Mount...
  • Parking
  • Family rooms

Good 10 Reviews 7.9

from $129.00 Show details »

Virginia Beach Family House Less Than 1 Mi to Golf Club! in Virginia Beach, USA

Virginia Beach Family House Less Than 1...

Holiday home in Virginia Beach near Chesapeake, Virginia
Located in Virginia Beach, 8.4 km from Mount Trashmore Park and 8.5 km from Virginia Beach National Golf Club, Virginia Beach Family House Less Than 1...
  • Parking
  • Internet facilities
  • Bath
  • TV
  • Air conditioning

Superb 9 Reviews 9.2

from $489.67 Show details »

Norfolk Home with Yard about 4 Mi to Downtown! in Norfolk, USA

Norfolk Home with Yard about 4 Mi to Dow...

Holiday home in Norfolk near Chesapeake, Virginia
Located in Norfolk, 13 km from Topgolf Virginia Beach, 18 km from Mount Trashmore Park and 27 km from Cape Henry Lighthouse, Norfolk Home with Yard ab...
  • Parking

no reviews

from $253.00 Show details »

Bright Chesapeake Home Near Shopping and Dining in Chesapeake, USA

Bright Chesapeake Home Near Shopping and...

Holiday home in Chesapeake, Virginia
Situated in Chesapeake, 25 km from Topgolf Virginia Beach, 30 km from Mount Trashmore Park and 32 km from Virginia Living Museum, Bright Chesapeake Ho...
  • Parking

Fabulous 4 Reviews 9.0

from $249.00 Show details »

Comfy King Bed Close to Everything in Virginia Beach, USA

Comfy King Bed Close to Everything

Holiday home in Virginia Beach near Chesapeake, Virginia , 4582 Marlwood Way
Comfy King Bed Close to Everything in Virginia Beach provides accommodation with free WiFi, 4.6 km from Topgolf Virginia Beach, 12 km from Virginia Be...
  • Parking
  • Internet facilities
  • Bath
  • TV
  • Air conditioning

Exceptional 2 Reviews 10.0

from $347.50 Show details »

Norfolk Garden HAFH in Norfolk, USA

Norfolk Garden HAFH

Holiday home in Norfolk near Chesapeake, Virginia , 1046 Hugo Street
Norfolk Oasis is situated in Norfolk, 11 km from Topgolf Virginia Beach, 16 km from Mount Trashmore Park, and 24 km from Cape Henry Lighthouse.
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 43 Reviews 9.0

from $190.00 Show details »

3-BR Home 3 mins to Airport + 11 mins to Beach in Norfolk, USA

3-BR Home 3 mins to Airport + 11 mins to...

Holiday home in Norfolk near Chesapeake, Virginia , 3349 Loam Street
Situated in Norfolk, 14 km from Mount Trashmore Park, 21 km from Virginia Beach National Golf Club and 22 km from Cape Henry Lighthouse, 3-BR Home 3 m...
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $160.67 Show details »

CHEERFUL 5 BEDROOM HOUSE CENTREALLY LOCATED . in Norfolk, USA

CHEERFUL 5 BEDROOM HOUSE CENTREALLY LOCA...

Holiday home in Norfolk near Chesapeake, Virginia , 7921 Merritt Street
Featuring garden views, CHEERFUL 5 BEDROOM HOUSE CENTREALLY LOCATED.
  • Parking
  • Family rooms

no reviews

from $351.00 Show details »

Virginia Vacation duplex house 1 in Virginia Beach, USA

Virginia Vacation duplex house 1

Holiday home in Virginia Beach near Chesapeake, Virginia , 4929 Rutherford Road
Set in Virginia Beach in the Virginia region, Virginia Vacation duplex house 1 offers accommodation with free WiFi and free private parking.
  • Parking

no reviews

from $216.00 Show details »

Va Beach Zen town house in Virginia Beach, USA

Va Beach Zen town house

Holiday home in Virginia Beach near Chesapeake, Virginia , 3320 Daytona Drive
Located in Virginia Beach and only 4.5 km from Mount Trashmore Park, Va Beach Zen town house provides accommodation with garden views, free WiFi and f...
  • Parking

Very good 6 Reviews 8.3

from $337.00 Show details »

Waterfront Paradise with Deck about half Mi to Beach in North Camellia Acres, USA

Waterfront Paradise with Deck about half...

Holiday home in North Camellia Acres near Chesapeake, Virginia
Located in North Camellia Acres, 500 metres from Ocean View Beach, 14 km from Topgolf Virginia Beach and 18 km from Mount Trashmore Park, Waterfront P...
  • Parking

no reviews

from $489.67 Show details »

Stately Norfolk Home with Fenced Yard Walk to Beach in Norfolk, USA

Stately Norfolk Home with Fenced Yard Wa...

Holiday home in Norfolk near Chesapeake, Virginia
Within 500 metres of Ocean View Beach and 13 km of Topgolf Virginia Beach, Stately Norfolk Home with Yard and Grill Walk to Beach offers free WiFi and...
  • Parking
  • Pets allowed
  • Internet facilities
  • Safety deposit box
  • Iron

Pleasant 2 Reviews 6.5

from $212.00 Show details »

Norfolk Home with Private Yard - Walk to Beach! in North Camellia Acres, USA

Norfolk Home with Private Yard - Walk to...

Holiday home in North Camellia Acres near Chesapeake, Virginia
Norfolk Home with Private Yard - Walk to Beach! is situated in North Camellia Acres, 13 km from Topgolf Virginia Beach, 18 km from Mount Trashmore Par...
  • Parking

no reviews

from $283.00 Show details »

Sunny Norfolk Duplex - Walk to Lake and Beach! in North Camellia Acres, USA

Sunny Norfolk Duplex - Walk to Lake and...

Holiday home in North Camellia Acres near Chesapeake, Virginia
Situated 13 km from Topgolf Virginia Beach, 18 km from Mount Trashmore Park and 20 km from Cape Henry Lighthouse, Sunny Norfolk Duplex - Walk to Lake ...
  • Parking

Superb 6 Reviews 9.5

from $230.00 Show details »

Bright Norfolk Home Less Than Half Mi Stroll to Beach in North Camellia Acres, USA

Bright Norfolk Home Less Than Half Mi St...

Holiday home in North Camellia Acres near Chesapeake, Virginia
Set in North Camellia Acres, 600 metres from Ocean View Beach and 1.5 km from Community Beach Park, Bright Norfolk Home Less Than Half Mi Stroll to Be...
  • Parking

Exceptional 4 Reviews 10.0

from $160.00 Show details »

Classic Chesapeake Beachside Cottage with Porch! in Norfolk, USA

Classic Chesapeake Beachside Cottage wit...

Holiday home in Norfolk near Chesapeake, Virginia
Classic Chesapeake Beachside Cottage with Porch! is a beachfront property located in Norfolk, 100 metres from Ocean View Beach and 2.1 km from Communi...
  • Parking

Superb 2 Reviews 9.5

from $368.33 Show details »

Beachfront Norfolk Paradise Outdoor Shower! in North Camellia Acres, USA

Beachfront Norfolk Paradise Outdoor Show...

Holiday home in North Camellia Acres near Chesapeake, Virginia
Located in North Camellia Acres, just a few steps from Ocean View Beach, Beachfront Norfolk Paradise Outdoor Shower! provides beachfront accommodation...
  • Parking

no reviews

from $354.00 Show details »

Charming Waterfront Cabin Cabin in Norfolk, USA

Charming Waterfront Cabin Cabin

Holiday home in Norfolk near Chesapeake, Virginia
Charming Waterfront Cabin Cabin is located in Norfolk, 1.4 km from Ocean View Beach Park, 1.7 km from Sarah Constant Beach Park, as well as 1.8 km fro...
  • Parking
  • Pets allowed
  • Internet facilities
  • Shower
  • Bath

no reviews

from $368.19 Show details »

Manor and Mutts #1 cottage in Norfolk, USA

Manor and Mutts #1 cottage

Holiday home in Norfolk near Chesapeake, Virginia
Located in Norfolk in the Virginia region, Manor and Mutts #1 cottage features a patio and sea views.
  • Parking
  • Pets allowed

Good 3 Reviews 7.7

from $482.88 Show details »

Charming Suffolk Cottage with Riverside Views in Suffolk, USA

Charming Suffolk Cottage with Riverside...

Holiday home in Suffolk near Chesapeake, Virginia
Situated 42 km from Topgolf Virginia Beach, 47 km from Mount Trashmore Park and 24 km from Riverfront Golf Club, Charming Suffolk Cottage with Riversi...
  • Parking

no reviews

from $117.00 Show details »

Charming Hampton Home with Yard 2 Mi to Beach! in Hampton, USA

Charming Hampton Home with Yard 2 Mi to...

Holiday home in Hampton near Chesapeake, Virginia
Located in Hampton, 43 km from Busch Gardens & Water Country and 20 km from Virginia Living Museum, Charming Hampton Home with Yard, 2 Mi to Beach! pr...
  • Parking

Superb 4 Reviews 9.5

from $329.00 Show details »

Ra15 609 - Endless Summer Cabin in Virginia Beach, USA

Ra15 609 - Endless Summer Cabin

Holiday home in Virginia Beach near Chesapeake, Virginia
Ra15 609 - Endless Summer Cabin is situated in Virginia Beach, 2.3 km from Croatan Beach, 1.2 km from The Virginia Beach Convention Center, as well as...
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • Shower
  • Bath

no reviews

from $198.00 Show details »

Sea La Vie in Virginia Beach, USA

Sea La Vie

Holiday home in Virginia Beach near Chesapeake, Virginia
Situated in Virginia Beach, 1.3 km from Viginia Beach and 1.8 km from Croatan Beach, Sea La Vie offers free WiFi and air conditioning.
  • Parking
  • Pets allowed

no reviews

from $419.71 Show details »

Number of Holiday homes in Chesapeake 118
Number of guest ratings 10309
Average price per night $370.45
Lowest price per night $117.00
Highest price per night $640.97

Most popular Holiday-homes in Chesapeake

The most popular Holiday-homes in Chesapeake based on average guest rating (Top 10).

Cheapest Holiday-homes in Chesapeake

The cheapest Holiday-homes in Chesapeake based on room rate per night (Top 10).

Most booked Holiday-homes in Chesapeake

The most booked Holiday-homes in Chesapeake based on popularity with guests (Top 10).

Holiday homes in Chesapeake (Virginia), comfortable and familiar

Staying in a holiday or vacation home in Chesapeake can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chesapeake for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chesapeake should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com