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

House Rentals in Chesapeake

Find 647 available offers from 7 partners
Chesapeake
Anytime
Guests
Ukraine Crisis Relief – Information to find and offer accommodations. Learn more

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

Show all 647 properties
Save up to 64%

Best Vacation Home Deals in Chesapeake

House Greenbrier West
May 6 - May 13
-49%
$691
$350 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Greenbrier West
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Western Branch North
Sep 23 - Sep 30
-36%
$329
$209 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Western Branch North with Grill
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Western Branch North
Dec 16 - Dec 23
-64%
$477
$170 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful Vacation Home in Western Branch North
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal

Find a vacation rental fitting your expectations among the 647 great accommodations from numerous providers in Chesapeake. HomeToGo, a vacation rental search engine, instantly compares all of these offers so you can save up to 71%!

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Chesapeake

Condo Indian River
Jul 22 - Jul 29
$319 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Indian River with Indoor Pool
4.7
"Outstanding" (11 ratings)
Indian River, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
Condo Greenbrier West
Jul 9 - Jul 16
$250 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Quiet Condo in Greenbrier West + Beautiful View
5.0
"Excellent" (4 ratings)
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Indian River
Sep 8 - Sep 15
-32%
$324
$219 per night
House ∙ 6 guests ∙ 1 bedroom
Family Friendly Entire House in Indian River with Free Parking
5.0
"Excellent" (2 ratings)
Indian River, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals in Chesapeake

Find your perfect vacation rental in Chesapeake: from $66 per night

House Greenbrier West
Aug 6 - Aug 13
$130 per night
House ∙ 5 guests ∙ 3 bedrooms
Vacation Home in Greenbrier West
4.0
"Very good" (1 rating)
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Greenbrier West
May 6 - May 13
-49%
$690
$350 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Greenbrier West
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Pleasant Grove West
Mar 16 - Mar 23
$114 per night
House ∙ 6 guests ∙ 3 bedrooms
Great Vacation Home in Pleasant Grove West with Yard & Grill
5.0
"Excellent" (3 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
Condo Indian River
Jul 22 - Jul 29
$319 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Indian River with Indoor Pool
4.7
"Outstanding" (11 ratings)
Indian River, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
Condo Greenbrier West
Jul 9 - Jul 16
$250 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Quiet Condo in Greenbrier West + Beautiful View
5.0
"Excellent" (4 ratings)
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Western Branch North
Sep 23 - Sep 30
-36%
$329
$209 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Western Branch North with Grill
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Indian River
Jul 14 - Jul 21
$185 per night
House ∙ 2 guests ∙ 3 bedrooms
Pleasant Vacation Home in Indian River
Indian River, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Western Branch North
Sep 23 - Sep 30
-64%
$563
$172 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful Vacation Home in Western Branch North
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Western Branch North
May 6 - May 13
-50%
$303
$150 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Western Branch North with Grill
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
See all offers
Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Chesapeake

House Greenbrier West
Aug 6 - Aug 13
$130 per night
House ∙ 5 guests ∙ 3 bedrooms
Vacation Home in Greenbrier West
4.0
"Very good" (1 rating)
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
House Pleasant Grove West
Dec 16 - Dec 23
$114 per night
House ∙ 6 guests ∙ 3 bedrooms
Great Vacation Home in Pleasant Grove West with Yard & Grill
5.0
"Excellent" (3 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal
Apartment Indian River
Apr 15 - Apr 22
-27%
$225
$165 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Pleasant Apartment in Indian River with Seasonal Pool
Indian River, Chesapeake, Virginia, United States
Details
Vrbo
View deal
View deal

Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Chesapeake rental with full kitchen.

House Kitchen Greenbrier West
Aug 6 - Aug 13
$130 per night
House ∙ 5 guests ∙ 3 bedrooms
Vacation Home in Greenbrier West
4.0
"Very good" (1 rating)
Greenbrier West, Chesapeake, Virginia, United States
Kitchen
Details
Vrbo
View deal
View deal
House Kitchen Pleasant Grove West
Dec 16 - Dec 23
$114 per night
House ∙ 6 guests ∙ 3 bedrooms
Great Vacation Home in Pleasant Grove West with Yard & Grill
5.0
"Excellent" (2 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Kitchen
Details
Vrbo
View deal
View deal
Condo Kitchen Indian River
Jul 22 - Jul 29
$319 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Indian River with Indoor Pool
4.7
"Outstanding" (11 ratings)
Indian River, Chesapeake, Virginia, United States
Kitchen
Details
Vrbo
View deal
View deal
See all offers

Vacation rentals with Wi-Fi

Stay connected while traveling and book a Chesapeake accommodation with high-speed internet.

Condo Internet Greenbrier West
Jul 9 - Jul 16
$250 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Quiet Condo in Greenbrier West + Beautiful View
5.0
"Excellent" (4 ratings)
Greenbrier West, Chesapeake, Virginia, United States
Internet
Details
Vrbo
View deal
View deal
House Internet Western Branch North
Dec 16 - Dec 23
-61%
$439
$171 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful Vacation Home in Western Branch North
Western Branch North, Chesapeake, Virginia, United States
Internet
Details
Vrbo
View deal
View deal
Condo Internet Indian River
Jul 8 - Jul 15
$258 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Indian River with Indoor Pool
Indian River, Chesapeake, Virginia, United States
Internet
Details
Vrbo
View deal
View deal
See all offers

Vacation rentals and apartments with air conditioning

Keep cool during your trip to Chesapeake and book a vacation rental with air conditioning.

Condo Air conditioning Indian River
Mar 29 - Apr 5
-34%
$258
$169 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Indian River with Botanical Garden
4.0
"Very good" (2 ratings)
Indian River, Chesapeake, Virginia, United States
Air conditioning
Details
Vrbo
View deal
View deal
Apartment Air conditioning South Norfolk
Jul 22 - Jul 29
$135 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in South Norfolk with Yard & Grill + Waterfront Views
South Norfolk, Chesapeake, Virginia, United States
Air conditioning
Details
Vrbo
View deal
View deal
House Air conditioning Indian River
Sep 8 - Sep 15
-28%
$306
$219 per night
House ∙ 6 guests ∙ 1 bedroom
Family Friendly Entire House in Indian River with Free Parking
5.0
"Excellent" (2 ratings)
Indian River, Chesapeake, Virginia, United States
Air conditioning
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities in Chesapeake

  • Internet (628)
  • TV (579)
  • Air conditioning (578)
  • Microwave (517)
  • No pets (348)
  • No smoking (347)
  • Pool (305)
  • Kitchen (263)
  • Wheelchair access (173)
  • Grill (154)
  • Crib (130)
  • Dishwasher (123)

Nearly half of the rentals offer a pool, which makes Chesapeake an excellent vacation destination for people looking to spend vacation poolside. Additionally, more House rental have pools than any other property type. They are an excellent choice if you go in a group of 8, as that is the number of people they can usually accommodate. If you would also like to be close to the water, a few of the rentals providing a pool are located within 2 miles of the waterfront.

7-Day Weather Forecast in Chesapeake

Sun, 26 Mar
73°
59°

0%

9 h

8 mi/h

Mon, 27 Mar
62°
53°

10%

1 h

6 mi/h

Tue, 28 Mar
62°
53°

0%

3 h

8 mi/h

Wed, 29 Mar
57°
42°

0%

11 h

7 mi/h

Thu, 30 Mar
68°
46°

0%

6 h

9 mi/h

Fri, 31 Mar
64°
59°

15%

0 h

13 mi/h

Sat, 1 Apr
78°
64°

15%

0 h

11 mi/h

Where to find the best food in Chesapeake?

What to Eat in Chesapeake

No matter what you want to eat and drink, Chesapeake has a little bit of everything to delight your taste buds. Wicker’s Crab Pot Seafood is the place in town to savor ocean delicacies. Favorites include the crab dip, blackened tuna tacos, and oysters served with drawn butter.

Modern and stylish, The Butcher’s Son is ideal for romantic dates. Start your gastronomic experience with some seafood nachos or honey mesquite pork belly, before moving on to delicious cuts of humanely raised, hormone-free beef and tasty salads. There's also event rooms for larger groups.

For tasty sandwiches, burgers, and soups in a homey setting, Pop’s Diner is a great pick. The friendly staff here make delectable specialty sandwiches, with turkey, cranberry, and brie on a buttered croissant the most popular. Breakfasts are fantastic here—try their blueberry pancakes.

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.

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.

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.

What are the best events and festivals in Chesapeake?

A Variety of Festivals

Chesapeake hosts fabulous family-friendly festivals throughout the year. The Annunciation Greek Orthodox Cathedral hosts the Norfolk Greek Festival in mid-May. Visitors get a taste of Greece through authentic food, traditional Greek dancing, and unique arts and crafts. Tours of the cathedral and its religious icons are also available.

If you’re visiting in early June, Norfolk's Harborfest is a showcase of the region's character. It's one of Virginia's longest-running events, with its renowned Parade of Sail featuring hundreds of military vessels, sailing craft, antique boats, cruisers, and more. Various musical acts and fireworks displays add energy to the festival.

The last week of July is time for the Blue Crab Festival. Organized by the South Norfolk Ruritan Club, this event celebrates the local crustacean delicacy. All-you-can-eat steamed crab, barbecued pork, and various alcoholic and non-alcoholic beverages are part of the spread. There's also live music for this uniquely fun gathering.

Information about vacation rentals in Chesapeake

🏡 Vacation rentals 647 properties
💳 Possible discounts up to 71%
🌙 Nightly prices starting at $66
⭐ Popular amenities Internet, TV and Air conditioning
🐾 Pet friendly accommodations 68 properties
🏊 Vacation rentals with pools 344 properties

Frequently Asked Questions

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

The average accommodation in Chesapeake is priced at $66 per night. If you would like to stay in a house rental, the average price is $376 per night. A apartment rental Chesapeake will cost $214 per night on average.

How many vacation homes are available for booking in Chesapeake?

There are 647 rentals in Chesapeake to browse and book for your next trip.

What amenities are most popular for vacation rentals in Chesapeake?

Usually travelers search for TV, Internet, and Air conditioning when booking a vacation rental in Chesapeake.

How many vacation homes with a pool are in Chesapeake?

Browse 344 vacation rentals available in Chesapeake.

Are dogs allowed in vacation rentals in Chesapeake?

Absolutely, currently there are 68 rentals in Chesapeake that allow pets , with an average nightly rate of $219.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Chesapeake TripAdvisor Vacation Rentals in Chesapeake Vrbo Vacation Rentals in Chesapeake VacationRentals.com Vacation Rentals in Chesapeake HouseTrip Vacation Rentals in Chesapeake FlipKey Vacation Rentals in Chesapeake Homestay.com Vacation Rentals in Chesapeake Only-apartments Vacation Rentals in Chesapeake Interhome Vacation Rentals in Chesapeake Novasol Vacation Rentals in Chesapeake HomeEscape Vacation Rentals in Chesapeake

Vacation Destinations Near Chesapeake

Top Vacation Ideas

Explore More Vacation Ideas

image-tag