Vacation rentals in Chesapeake - HomeToGo base64Hash Vacation rentals in Chesapeake - HomeToGo

Vacation rentals in Chesapeake

Browse 687 available vacation homes and compared across 10 trusted partners
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Top 15 most Recommended Vacation Rentals in Chesapeake

Discover your ideal Chesapeake vacation rental with real-time comparisons of 693 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Western Branch North
Apartment ∙ 4 guests ∙ 2 bedrooms

Fully equipped ample rental apartment | Suitable for remote work | Dogs allowed

Western Branch North, Chesapeake, Virginia, United States
from $127
per night
from $127
per night
View deal
House Indian River
House ∙ 2 guests ∙ 3 bedrooms

Children-friendly pleasant vacation home | Perfect for remote work

Indian River, Chesapeake, Virginia, United States
from $283
per night
Very good(6 ratings)
from $283
per night
View deal
Apartment Western Branch North
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with garden

Western Branch North, Chesapeake, Virginia, United States
from $102
per night
from $102
per night
View deal
Condo Indian River
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with grill, hot tub & pool

Indian River, Chesapeake, Virginia, United States
from $410
per night
Excellent(16 ratings)
from $410
per night
View deal
House Western Branch North
House ∙ 8 guests ∙ 4 bedrooms

House with 4 rooms for 8 persons

Western Branch North, Chesapeake, Virginia, United States
from $294
per night
from $294
per night
View deal
House South Norfolk
House ∙ 5 guests ∙ 3 bedrooms

Vacation home | Dogs allowed

South Norfolk, Chesapeake, Virginia, United States
from $118
per night
Outstanding(2 ratings)
from $118
per night
View deal
House Indian River
House ∙ 8 guests ∙ 4 bedrooms

House with barbeque, patio & yard | Good for workation

Indian River, Chesapeake, Virginia, United States
from $224
per night
Very good(6 ratings)
from $224
per night
View deal
House Greenbrier West
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped wonderful house with grill & private pool | Pet-friendly

Greenbrier West, Chesapeake, Virginia, United States
from $785
per night
from $785
per night
View deal
Apartment Western Branch North
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with 2 rooms for 4 persons

Western Branch North, Chesapeake, Virginia, United States
from $118
per night
from $118
per night
View deal
House Chesapeake
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house with garden & pool | Lake view

Chesapeake, Virginia, United States
from $359
per night
Outstanding(4 ratings)
from $359
per night
View deal
House Western Branch North
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque & patio

Western Branch North, Chesapeake, Virginia, United States
from $219
per night
Excellent(14 ratings)
from $219
per night
View deal
Apartment Western Branch North
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with yard, patio & jacuzzi | Suitable for remote work

Western Branch North, Chesapeake, Virginia, United States
from $82
per night
Very good(1 rating)
from $82
per night
View deal
House Western Branch South
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with 4 rooms for 9 persons

Western Branch South, Chesapeake, Virginia, United States
from $301
per night
Very good(34 ratings)
from $301
per night
View deal
House Indian River
House ∙ 4 guests ∙ 2 bedrooms

Child-friendly house with grill | Dogs allowed

Indian River, Chesapeake, Virginia, United States
from $187
per night
Outstanding(7 ratings)
from $187
per night
View deal
Condo South Norfolk
Condo ∙ 2 guests ∙ 1 bedroom

Condo with 1 room for 2 persons

South Norfolk, Chesapeake, Virginia, United States
from $58
per night
from $58
per night
View deal

Vacation Rentals With Fireplaces

House  South Norfolk
from $262
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped nice house with barbeque

5.0
Outstanding(31 ratings)
South Norfolk, Chesapeake, Virginia, United States
Fireplace
View deal
House  Western Branch North
from $255
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly beautiful vacation home

4.4
Very good(19 ratings)
Western Branch North, Chesapeake, Virginia, United States
Fireplace
View deal
House  Western Branch South
from $197
per night
House ∙ 6 guests ∙ 3 bedrooms

House with 3 rooms for 6 persons

4.7
Excellent(25 ratings)
Western Branch South, Chesapeake, Virginia, United States
Fireplace
View deal
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Budget-friendly rental options

Enjoy affordable vacation rentals in Chesapeake offering exceptional value for money

Motel Deep Creek North
from $81
per night
Motel ∙ 5 guests ∙ 1 bedroom

Motel for 5 persons

Deep Creek North, Chesapeake, Virginia, United States
View deal
Motel Western Branch North
from $80
per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

Western Branch North, Chesapeake, Virginia, United States
View deal
Motel Western Branch South
from $73
per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.4
(223 ratings)
Western Branch South, Chesapeake, Virginia, United States
View deal

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Popular Features & Amenities in Chesapeake

  • Pet-friendly (168)
  • Pool (297)
  • WiFi (625)
  • TV (584)
  • Air conditioning (631)
  • Kitchen (255)
  • Washing machine (324)
  • Parking (6)
  • Grill (138)
  • Microwave (495)
  • Fishing (6)
  • Dishwasher (108)

You can find a large selection of accommodations to choose from if you are looking for an accommodation including a pool in Chesapeake. Hotel room with pools in Chesapeake are a excellent choice for groups of 4 and cost, on average, $166 per night. You can also find and book a vacation rental offering a pool near the water, which is the case for a few of the rentals there.

Cozy Chesapeake Vacation Rentals Amidst History and Nature

Located along the Intracoastal Waterway on Virginia’s Atlantic coast, Chesapeake boasts a host of other extensive waterways ranging from lakes to rivers and canals. Relax in a charming house rental, or one of the city's many condo rentals, and experience numerous outdoor activities such as birdwatching and hiking. If you choose to stay in the city, museums and diverse dining options abound.

What are the best activities for families in Chesapeake?

Fun Activities for the Family

Chesapeake's family-friendly attractions mix nature with urban fun. Take a guided cruise on the local waters from Hampton Roads or Norfolk. It's a great way to enjoy some sunshine and sea breezes. Tours cover various areas and usually focus on the area's maritime heritage.

Visit the Chesapeake Municipal Center's planetarium, and delve into the wonders of the universe. The first of its kind to be built by a public school system, this facility offers an array of free public programs such as telescope observations. Shows on Thursday are free.

The Town Point Park area provides plenty of opportunities for fun. There's plenty of room to play and picnic amidst its spacious lawns and fountains. Visit the Nauticus maritime museum, with the USS Wisconsin battleship moored next to it. In the summer, various open-air concerts and festivals are held here.

What are the best places to discover the arts and culture of Chesapeake?

Unique Local Art and Culture

Chesapeake has a lively artistic and cultural scene. If you like having a hand in your art, then head to AR Workshop Chesapeake. It’s a family-friendly studio that offers lessons on how you can create objects such as canvas tote bags and framed signs. All the materials you'll need are available.

Spend a day at the Virginia Museum of Contemporary Art for an extensive collection of art, including paintings, sculptures, photos, and video installations from local and international artists. There's also studio lessons and workshops on photography, painting, and ceramics.

Another interesting museum is the Chrysler Museum of Art in nearby Norfolk. It houses over 30,000 pieces of art, and a working glassmaking studio that's the only one of its kind in the Mid-Atlantic region. Best of all, parking and admission are free.

Where are the unique attractions in Chesapeake?

What to See and Do in Chesapeake

Chesapeake is blessed with natural beauty in and around the city for the whole family to enjoy. If being out in nature interests you, then check out the Great Dismal Swamp National Wildlife Refuge. You'll come into contact with numerous species of wildlife including butterflies, red foxes, and flying squirrels.

Head to the Chesapeake Arboretum to marvel at the staggering number of trees on site. Relax on the green grass, or take a self-guided tour on the trails as you commune with nature. A propagation nursery and greenhouse provide glimpses of the ongoing conservation efforts here.

The Northwest River Park along Indian Creek Rd provides a break from urban life, with its nature reserve and fantastic recreational facilities. Whether you want to swim, fish, or play a round of disc or mini golf, the park has something for everyone to enjoy.

Information about vacation rentals in Chesapeake

🏡 Vacation rentals available 693 rentals
🌙 Nightly prices starting at $61
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 175 homes
🏊 Vacation rentals with pools 297 homes

Frequently Asked Questions

What is the typical price per night for a vacation home in Chesapeake?

On average, vacation rentals in Chesapeake cost around $61 per night. Average prices for house rentals are $381 per night. Apartment rentals in Chesapeake cost on average $144 per night.

How many vacation rentals are available for booking in Chesapeake?

There are 693 rentals in Chesapeake to choose from and book for your trip.

What are the most popular amenities for vacation homes in Chesapeake?

Three most popular amenities for vacation home rentals in Chesapeake include accommodations with: Pets allowed, Pool, and Internet.

How many vacation rentals with pools are there in Chesapeake?

Choose from 297 vacation rentals available in Chesapeake.

Are pets allowed in vacation homes in Chesapeake?

Finding a vacation home in Chesapeake that allows dogs is possible, with 175 pet-friendly available.

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