House Rentals in Chesapeake - HomeToGo base64Hash House Rentals in Chesapeake - HomeToGo

House Rentals in Chesapeake

Find 732 available offers from 9 partners
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1 guest
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Recommended vacation rentals in Chesapeake

Find your perfect vacation rental in Chesapeake from just $67 per night!

House South Norfolk
May 10 - May 17
House ∙ 8 guests ∙ 3 bedrooms

Pleasant Vacation Home with Barbecue | Pets Allowed

South Norfolk, Chesapeake, Virginia, United States
$295
per night
Outstanding(27 ratings)
$295
per night
View deal
House Western Branch South
Jun 21 - Jun 28
Free cancellation
House ∙ 8 guests ∙ 4 bedrooms

House with 4 Rooms for 8 Persons

Western Branch South, Chesapeake, Virginia, United States
$634
per night
$634
per night
View deal
House Chesapeake
-69%
Mar 13 - Mar 20
House ∙ 11 guests ∙ 6 bedrooms

Fully Equipped House with Terrace & BBQ | Pet-Friendly

Chesapeake, Virginia, United States
$916$626
per night
Outstanding(13 ratings)
$916$626
per night
View deal
House Indian River
Mar 22 - Mar 29
House ∙ 6 guests ∙ 3 bedrooms

Children-Friendly House with Yard | Dogs Allowed

Indian River, Chesapeake, Virginia, United States
$182
per night
Excellent(11 ratings)
$182
per night
View deal
Apartment Deep Creek South
-50%
Jun 14 - Jun 21
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment with Terrace, BBQ & Garden

Deep Creek South, Chesapeake, Virginia, United States
$168$91
per night
Outstanding(64 ratings)
$168$91
per night
View deal
Farmhouse Pleasant Grove West
Jul 19 - Jul 26
Farmhouse ∙ 5 guests ∙ 1 bedroom

Children-Friendly Farm with Private Pool, Garden & Terrace | Dogs Allowed

Pleasant Grove West, Chesapeake, Virginia, United States
$217
per night
Outstanding(10 ratings)
$217
per night
View deal
House Western Branch North
-55%
Mar 22 - Mar 29
House ∙ 8 guests ∙ 5 bedrooms

Family-Friendly Beautiful Vacation Home

Western Branch North, Chesapeake, Virginia, United States
$643$482
per night
Very good(8 ratings)
$643$482
per night
View deal
House Indian River
May 17 - May 24
House ∙ 2 guests ∙ 3 bedrooms

Family-Friendly Big Vacation Home | Good for Workation

Indian River, Chesapeake, Virginia, United States
$295
per night
Very good(6 ratings)
$295
per night
View deal
Condo Indian River
May 10 - May 17
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Condo with Pool, Barbecue & Yard

Indian River, Chesapeake, Virginia, United States
$358
per night
Excellent(16 ratings)
$358
per night
View deal
Apartment Indian River
-29%
Mar 13 - Mar 20
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with Pool & Grill

Indian River, Chesapeake, Virginia, United States
$279$197
per night
Outstanding(4 ratings)
$279$197
per night
View deal
House Greenbrier West
Aug 2 - Aug 9
Free cancellation
House ∙ 10 guests ∙ 4 bedrooms

House with Hot Tub | Pets Are Welcome

Greenbrier West, Chesapeake, Virginia, United States
$866
per night
$866
per night
View deal
House Greenbrier West
Jul 12 - Jul 19
House ∙ 10 guests ∙ 4 bedrooms

Fully Equipped Nice House with Private Pool & Grill | Pets Are Welcome

Greenbrier West, Chesapeake, Virginia, United States
$759
per night
$759
per night
View deal
House Indian River
May 17 - May 24
House ∙ 4 guests ∙ 2 bedrooms

Children-Friendly House | Pets Are Welcome

Indian River, Chesapeake, Virginia, United States
$154
per night
Outstanding(2 ratings)
$154
per night
View deal
House Western Branch South
Mar 22 - Mar 29
House ∙ 6 guests ∙ 3 bedrooms

House with 3 Rooms for 6 Persons

Western Branch South, Chesapeake, Virginia, United States
$213
per night
Outstanding(3 ratings)
$213
per night
View deal
House Western Branch South
-91%
Mar 15 - Mar 22
Free cancellation
House ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Vacation Home with Garden

Western Branch South, Chesapeake, Virginia, United States
$3,110$352
per night
Outstanding(1 rating)
$3,110$352
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Indian River
Feb 22 - Mar 1
-28%
$324
$233
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with Hot Tub, Pool & BBQ

Indian River, Chesapeake, Virginia, United States
Free cancellation
Air conditioning
View deal
Motel  Indian River
Mar 22 - Mar 29
$67
per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel

Indian River, Chesapeake, Virginia, United States
Free cancellation
Air conditioning
View deal
House  Indian River
Mar 22 - Mar 29
$182
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-Friendly House with Yard | Dogs Allowed

4.5
Excellent(11 ratings)
Indian River, Chesapeake, Virginia, United States
Air conditioning
View deal
See all offers

Best Vacation Home Deals in Chesapeake

Save up to 43%

Apartment Indian River
Feb 15 - Feb 22
-30%
$227
$159
per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment with Barbecue & Pool

Indian River, Chesapeake, Virginia, United States
View deal
House Western Branch North
Aug 2 - Aug 9
-28%
$375
$270
per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely Vacation Home with 2 Rooms for 4 Persons

Western Branch North, Chesapeake, Virginia, United States
Free cancellation
View deal
Studio flat Indian River
Jan 18 - Jan 25
-43%
$253
$144
per night
Studio flat ∙ 2 guests ∙ 1 bedroom

Studio with Jacuzzi, Barbeque & Pool

Indian River, Chesapeake, Virginia, United States
View deal

Explore the 732 properties listed in Chesapeake and discover the ideal accommodation for your vacation. By comparing these vacation rentals, HomeToGo features the lowest prices as well as the most popular properties in Chesapeake.

Budget-friendly Vacation Rentals in Chesapeake

Find Fantastic yet Inexpensive Offers

House Western Branch South
Jun 21 - Jun 28
$552
per night
House ∙ 8 guests ∙ 5 bedrooms

Fully Equipped Wonderful House with Yard & Patio

5.0
Outstanding(3 ratings)
Western Branch South, Chesapeake, Virginia, United States
View deal
Apartment Indian River
May 17 - May 24
$179
per night
Apartment ∙ 3 guests ∙ 1 bedroom

Nice Holiday Apartment with Barbeque & Pool

Indian River, Chesapeake, Virginia, United States
View deal
Motel Indian River
Mar 22 - Mar 29
$67
per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel

Indian River, Chesapeake, Virginia, United States
Free cancellation
View deal

Top-Rated Rentals and Accommodations in Chesapeake

Book Vacation Rental Offers with the Highest User Rating

House Western Branch South
Jun 14 - Jun 21
$322
per night
House ∙ 9 guests ∙ 4 bedrooms

House with 4 Rooms for 9 Persons

4.6
Excellent(16 ratings)
Western Branch South, Chesapeake, Virginia, United States
View deal
House Deep Creek North
from $231
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home | Pet-Friendly

4.5
Excellent(4 ratings)
Deep Creek North, Chesapeake, Virginia, United States
View deal
House Chesapeake
Jun 14 - Jun 21
$398
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully Equipped House with Garden & Pool | Lake View

5.0
Outstanding(2 ratings)
Chesapeake, Virginia, United States
View deal

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Popular Rental Amenities in Chesapeake

  • Pet-friendly (178)
  • Pool (331)
  • WiFi (676)
  • TV (621)
  • Air conditioning (693)
  • Kitchen (271)
  • Washing machine (297)
  • Parking (9)
  • Grill (140)
  • Microwave (505)
  • Fishing (12)
  • 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 11 and cost, on average, $183 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 732 rentals
💳 Possible discounts up to 44%
🌙 Nightly prices starting at $67
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 178 homes
🏊 Vacation rentals with pools 330 homes
226,425 reviews
Chesapeake vacation rentals have an average rating of 3.5/5 on 226,425 reviews left by travelers.

Frequently Asked Questions

What is the nightly price for a vacation rental in Chesapeake?

The average accommodation in Chesapeake is priced at $67 per night. Nightly prices for house rentals are $353 on average. Apartment rentals in Chesapeake cost $227 per night on average.

How many vacation rentals are available for booking in Chesapeake?

Currently there are 732 rentals in Chesapeake to browse and rent for your trip.

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

Most travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Chesapeake.

How many vacation rentals with a pool are there in Chesapeake?

Discover 330 vacation rentals available in Chesapeake for renting.

Are pets allowed in vacation homes in Chesapeake?

If traveling with a dog in Chesapeake, 24% of vacation rentals allow pets.

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