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

House Rentals in Chesapeake

Find 477 available offers from 15 partners
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Apartment
House
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
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.

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Save up to 68%

Best Vacation Home Deals in Chesapeake

Motel Deep Creek North
Nov 19 - Nov 26
-68%
$176
$56 per night
Motel ∙ 3 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
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Motel Deep Creek North
Nov 19 - Nov 26
-67%
$181
$60 per night
Motel ∙ 5 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
Details
HomeToGo
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Find a vacation rental fitting your expectations among the 477 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 83%!

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Top-Rated Rentals and Accommodations in Chesapeake

House Great Bridge
Jan 22 - Jan 29
$300 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (1 rating)
Great Bridge, Chesapeake, Virginia, United States
Free cancellation
Details
Vrbo
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Apartment Indian River
Jan 22 - Jan 29
$312 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (5 ratings)
Indian River, Chesapeake, Virginia, United States
Free cancellation
Details
Vrbo
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Recommended Vacation Rentals in Chesapeake

Find your perfect vacation rental in Chesapeake: from $53 per night

Apartment Indian River
$56 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Details
trivago’s partner
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Motel Greenbrier West
$60 per night
Motel ∙ 4 guests ∙ 1 bedroom
Greenbrier West, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Western Branch North
$84 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Western Branch North
$84 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Western Branch South
$53 per night
Motel ∙ 4 guests ∙ 1 bedroom
Western Branch South, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Deep Creek North
$69 per night
Motel ∙ 3 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Western Branch South
$53 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch South, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Western Branch South
$53 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch South, Chesapeake, Virginia, United States
Details
HomeToGo
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Motel Western Branch South
$53 per night
Motel ∙ 4 guests ∙ 1 bedroom
Western Branch South, Chesapeake, Virginia, United States
Details
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Vacation rentals with Wi-Fi

Motel Internet Deep Creek North
Jun 11 - Jun 18
$110 per night
Motel ∙ 14 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
Free cancellation
Internet
Details
Expedia
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Motel Internet Western Branch North
May 21 - May 28
-19%
$91
$74 per night
Motel ∙ 14 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
Free cancellation
Internet
Details
Expedia
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Motel Internet Western Branch North
May 21 - May 28
-19%
$100
$82 per night
Motel ∙ 4 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
Internet
Details
HomeToGo
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Vacation rentals and apartments with air conditioning

Motel Aircondition Deep Creek North
Nov 12 - Nov 19
-68%
$172
$56 per night
Motel ∙ 3 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
Aircondition
Details
HomeToGo
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Motel Aircondition Deep Creek North
Nov 12 - Nov 19
-66%
$177
$60 per night
Motel ∙ 5 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
Aircondition
Details
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Popular Rental Amenities in Chesapeake

  • Internet (528)
  • Air conditioning (431)
  • TV (404)
  • Microwave (361)
  • No smoking (297)
  • Pool (252)
  • No pets (208)
  • Wheelchair access (143)
  • Kitchen (141)
  • Grill (113)
  • Crib (100)
  • Washer (58)

Nearly half of the rentals offer a pool, which makes Chesapeake an excellent vacation destination for people looking to spend vacation poolside. Additionally, more Apartment rentals have pools than any other property type. They are an excellent choice if you go in a group of 5, 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, 22 May
89°
73°

15%

4 h

8 mi/h

Mon, 23 May
69°
66°

15%

3 h

11 mi/h

Tue, 24 May
68°
62°

0%

2 h

8 mi/h

Wed, 25 May
75°
64°

5%

4 h

7 mi/h

Thu, 26 May
80°
71°

15%

1 h

8 mi/h

Fri, 27 May
78°
73°

15%

1 h

12 mi/h

Sat, 28 May
75°
68°

15%

2 h

5 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.

Frequently Asked Questions

How much does it cost to rent a vacation rental in Chesapeake?

The average nightly price for vacation rentals in Chesapeake is $53.

How many vacation rentals are available to book in Chesapeake?

There are currently 467 vacation homes in Chesapeake to browse and book for your next trip.

What amenities are most popular for vacation homes in Chesapeake?

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

How many vacation rentals are in Chesapeake?

Discover 467 vacation rentals available to book in Chesapeake.

Are pets allowed in vacation rentals in Chesapeake?

Finding a cabin rental in Chesapeake that allows dogs is definitely possible, with 73 pet-friendly homes on offfer.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Chesapeake TripAdvisor Vacation Rentals in Chesapeake Vrbo Vacation Rentals in Chesapeake Airbnb Vacation Rentals in Chesapeake VacationRentals.com Vacation Rentals in Chesapeake HouseTrip Vacation Rentals in Chesapeake FlipKey Vacation Rentals in Chesapeake 9flats.com Vacation Rentals in Chesapeake PerfectPlaces.com Vacation Rentals in Chesapeake Homestay.com Vacation Rentals in Chesapeake Only-apartments Vacation Rentals in Chesapeake Interhome Vacation Rentals in Chesapeake Bedycasa Vacation Rentals in Chesapeake Novasol Vacation Rentals in Chesapeake HomeEscape Vacation Rentals in Chesapeake

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