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

House Rentals in Chesapeake

Find 642 available offers from 10 partners
Chesapeake
Anytime
Guests
Chesapeake
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Guests

Popular Filters to find the Perfect Home Rental in Chesapeake

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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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Vacation rentals with Wi-Fi

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

House  Chesapeake
Sep 20 - Sep 27
-38%
$369
$230 per night
House ∙ 11 guests ∙ 4 bedrooms

House in Chesapeake with Grill & Patio

5.0
Outstanding (6 ratings)
Chesapeake, Virginia, United States
Internet
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Farmhouse  Pleasant Grove West
Jun 30 - Jul 7
$189 per night
Farmhouse ∙ 5 guests ∙ 1 bedroom

Farm in Pleasant Grove West

5.0
Outstanding (1 rating)
Pleasant Grove West, Chesapeake, Virginia, United States
Internet
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House  Western Branch North
Aug 3 - Aug 10
$300 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Western Branch North with Grill

5.0
Outstanding (2 ratings)
Western Branch North, Chesapeake, Virginia, United States
Internet
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Apartments and vacation rentals with a kitchen

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

Condo  Indian River
Jun 30 - Jul 7
-38%
$361
$226 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Indian River with Indoor Pool

Indian River, Chesapeake, Virginia, United States
Kitchen
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House  Indian River
Aug 10 - Aug 17
$178 per night
House ∙ 6 guests ∙ 3 bedrooms

Family Friendly Entire House in Indian River with Free Parking

5.0
Outstanding (2 ratings)
Indian River, Chesapeake, Virginia, United States
Kitchen
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House  Pleasant Grove West
Sep 14 - Sep 21
$148 per night
House ∙ 6 guests ∙ 3 bedrooms

Great Vacation Home in Pleasant Grove West with Yard, Patio & Grill

5.0
Outstanding (19 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Kitchen
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Vacation rentals and apartments with air conditioning

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

Studio flat  Indian River
Jul 20 - Jul 27
$251 per night
Studio flat ∙ 3 guests ∙ 1 bedroom

Studio in Indian River with Seasonal Pool + City View

Indian River, Chesapeake, Virginia, United States
Free cancellation
Air conditioning
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House  Western Branch North
Aug 17 - Aug 24
$199 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Western Branch North

5.0
Outstanding (7 ratings)
Western Branch North, Chesapeake, Virginia, United States
Air conditioning
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House  Indian River
Aug 3 - Aug 10
$125 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Indian River

Indian River, Chesapeake, Virginia, United States
Air conditioning
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Best Vacation Home Deals in Chesapeake

Save up to 40%

Condo Indian River
Jul 1 - Jul 8
-21%
$274
$216 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Indian River with Indoor Pool

5.0
Outstanding (2 ratings)
Indian River, Chesapeake, Virginia, United States
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Condo Indian River
Jun 30 - Jul 7
-35%
$375
$244 per night
Condo ∙ 6 guests ∙ 1 bedroom

Condo in Indian River with Complimentary Parking

Indian River, Chesapeake, Virginia, United States
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Studio flat Indian River
Jun 30 - Jul 7
-40%
$340
$203 per night
Studio flat ∙ 2 guests ∙ 1 bedroom

Studio in Indian River with Indoor Pool + City View

Indian River, Chesapeake, Virginia, United States
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Find a vacation rental fitting your expectations among the 642 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 22%!

Recommended Vacation Rentals in Chesapeake

Find your perfect vacation rental in Chesapeake: from $72 per night

House Indian River
Jun 7 - Jun 14
$231 per night
House ∙ 2 guests ∙ 3 bedrooms

Pleasant Vacation Home in Indian River

4.0
Very good (6 ratings)
Indian River, Chesapeake, Virginia, United States
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House Western Branch North
Aug 10 - Aug 17
$259 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Western Branch North with Patio & Grill

4.5
Excellent (12 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Western Branch North
Aug 3 - Aug 10
$388 per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful Vacation Home in Western Branch North

4.0
Very good (6 ratings)
Western Branch North, Chesapeake, Virginia, United States
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Apartment Deep Creek South
Sep 7 - Sep 14
$72 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Deep Creek South with Grill, Patio & Yard

4.9
Outstanding (56 ratings)
Deep Creek South, Chesapeake, Virginia, United States
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House Indian River
Jul 6 - Jul 13
$350 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Indian River

4.8
Outstanding (10 ratings)
Indian River, Chesapeake, Virginia, United States
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Condo Indian River
Jul 7 - Jul 14
$284 per night
Condo ∙ 2 guests ∙ 1 bedroom

Nice Condo in Indian River with Indoor Pool

Indian River, Chesapeake, Virginia, United States
Free cancellation
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Condo Indian River
Jun 29 - Jul 6
$254 per night
Condo ∙ 4 guests ∙ 1 bedroom

Pleasant Condo in Indian River with Complimentary Parking

Indian River, Chesapeake, Virginia, United States
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House Deep Creek South
Aug 24 - Aug 31
$234 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Deep Creek South with Pool & Patio

5.0
Outstanding (1 rating)
Deep Creek South, Chesapeake, Virginia, United States
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Apartment Pleasant Grove West
Sep 7 - Sep 14
$94 per night
Apartment ∙ 4 guests ∙ 1 bedroom

House in Pleasant Grove West

Pleasant Grove West, Chesapeake, Virginia, United States
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Budget-friendly Vacation Rentals in Chesapeake

Find Fantastic yet Inexpensive Offers

Studio flat Indian River
Aug 3 - Aug 10
-26%
$340
$251 per night
Studio flat ∙ 3 guests ∙ 1 bedroom

Nice Studio in Indian River with Indoor Pool

Indian River, Chesapeake, Virginia, United States
Free cancellation
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House Western Branch South
Jun 28 - Jul 5
$675 per night
House ∙ 13 guests ∙ 4 bedrooms

Vacation Home in Western Branch South with Pool

4.3
Very good (14 ratings)
Western Branch South, Chesapeake, Virginia, United States
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House Western Branch North
Dec 8 - Dec 15
-59%
$370
$153 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Western Branch North

Western Branch North, Chesapeake, Virginia, United States
Free cancellation
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Top-Rated Rentals and Accommodations in Chesapeake

Book Vacation Rental Offers with the Highest User Rating

Apartment Indian River
Jul 1 - Jul 8
-18%
$239
$195 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Indian River with Complimentary Parking + City View

5.0
Outstanding (3 ratings)
Indian River, Chesapeake, Virginia, United States
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House Western Branch North
$167 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Western Branch North with Patio + Harbour View

4.7
Excellent (3 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Greenbrier West
$158 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Greenbrier West with Patio

4.8
Outstanding (7 ratings)
Greenbrier West, Chesapeake, Virginia, United States
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Popular Rental Amenities in Chesapeake

  • Pet-friendly (64)
  • Pool (295)
  • WiFi (610)
  • TV (577)
  • Air conditioning (617)
  • Kitchen (258)
  • Washing machine (290)
  • Parking (16)
  • Grill (141)
  • Microwave (513)
  • Fishing (10)
  • Dishwasher (114)

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 12, 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

Sat, 22 Jun
93°
89°

0%

6 h

9 mi/h

Sun, 23 Jun
91°
87°

0%

2 h

14 mi/h

Mon, 24 Jun
86°
77°

15%

1 h

7 mi/h

Tue, 25 Jun
89°
84°

10%

6 h

9 mi/h

Wed, 26 Jun
96°
96°

0%

5 h

10 mi/h

Thu, 27 Jun
100°
84°

15%

2 h

6 mi/h

Fri, 28 Jun
89°
87°

10%

6 h

9 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 available 642 rentals
💳 Possible discounts up to 22%
🌙 Nightly prices starting at $72
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 64 homes
🏊 Vacation rentals with pools 295 homes

Frequently Asked Questions

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

The nightly price of accommodations in Chesapeake starts at $72. If you’re interested in a house rental, the average price is $347 per night. A apartment rental Chesapeake will cost $210 per night on average.

How many vacation homes are available for booking in Chesapeake?

Currently there are 642 vacation rentals in Chesapeake to browse and book for your trip.

What amenities are most popular for vacation homes in Chesapeake?

If you're looking to book a vacation rental in Chesapeake, the most common amenities are: Pool, Pets allowed and Internet.

How many vacation rentals with pools are there in Chesapeake?

Chesapeake offers 295 Hotel room and Condo options available for booking.

Are pets allowed in vacation rentals in Chesapeake?

Absolutely, there are 64 vacation rentals in Chesapeake that allow dogs , with an average nightly rate of $207.

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