House Rentals in Chesapeake - HomeToGo base64Hash

House Rentals in Chesapeake

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Price per night

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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.

Best Vacation Home Deals in Chesapeake

Save up to 51%

Mar 23 - Mar 30

-50%

~~$300~~

$150 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

Details

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Nov 4 - Nov 11

-44%

~~$237~~

$133 per night

House ∙ 6 guests ∙ 3 bedrooms

Beautiful House in South Norfolk

5.0

Outstanding (5 ratings)

South Norfolk, Chesapeake, Virginia, United States

Details

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Sep 14 - Sep 21

-51%

~~$326~~

$159 per night

House ∙ 8 guests ∙ 4 bedrooms

Beautiful Vacation Home in Western Branch North

5.0

Outstanding (2 ratings)

Western Branch North, Chesapeake, Virginia, United States

Details

Vrbo

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Find a vacation rental fitting your expectations among the 638 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 46%!

Top-Rated Rentals and Accommodations in Chesapeake

Book Vacation Rental Offers with the Highest User Rating

Nov 3 - Nov 10

$66 per night

Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Deep Creek South with Grill & Yard

5.0

Outstanding (46 ratings)

Deep Creek South, Chesapeake, Virginia, United States

Details

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Aug 18 - Aug 25

$114 per night

House ∙ 6 guests ∙ 3 bedrooms

Great Vacation Home in Pleasant Grove West with Yard & Grill

5.0

Outstanding (13 ratings)

Pleasant Grove West, Chesapeake, Virginia, United States

Details

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Dec 16 - Dec 23

-33%

~~$280~~

$188 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

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Recommended Vacation Rentals in Chesapeake

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

Jun 22 - Jun 29

$660 per night

House ∙ 11 guests ∙ 4 bedrooms

Wonderful House in Greenbrier West with Grill & Pool

Greenbrier West, Chesapeake, Virginia, United States

Details

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Jul 14 - Jul 21

$244 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Western Branch South

4.4

Very good (5 ratings)

Western Branch South, Chesapeake, Virginia, United States

Details

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Mar 16 - Mar 23

$138 per night

House ∙ 6 guests ∙ 3 bedrooms

Entire Vacation Home in Western Branch South with Adequate Parking

4.3

Very good (4 ratings)

Western Branch South, Chesapeake, Virginia, United States

Details

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Oct 7 - Oct 14

-32%

~~$628~~

$427 per night

House ∙ 4 guests ∙ 4 bedrooms

Vacation Home in Western Branch South with Yard + Beautiful View

Western Branch South, Chesapeake, Virginia, United States

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Oct 20 - Oct 27

-29%

~~$192~~

$137 per night

House ∙ 6 guests ∙ 3 bedrooms

House in Western Branch North with Grill

4.4

Very good (8 ratings)

Western Branch North, Chesapeake, Virginia, United States

Details

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May 18 - May 25

$245 per night

House ∙ 8 guests ∙ 3 bedrooms

Nice House in South Norfolk with Grill + Ocean View

4.9

Outstanding (13 ratings)

South Norfolk, Chesapeake, Virginia, United States

Details

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Mar 2 - Mar 9

-40%

~~$225~~

$135 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in South Norfolk with Ample Parking

South Norfolk, Chesapeake, Virginia, United States

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Sep 14 - Sep 21

-51%

~~$222~~

$109 per night

House ∙ 4 guests ∙ 2 bedrooms

House in Western Branch North + Harbour View

Western Branch North, Chesapeake, Virginia, United States

Details

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Dec 2 - Dec 9

-66%

~~$341~~

$118 per night

House ∙ 8 guests ∙ 4 bedrooms

House in Western Branch North

Western Branch North, Chesapeake, Virginia, United States

Free cancellation

Details

Evolve

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Budget-friendly Vacation Rentals in Chesapeake

Find Fantastic yet Inexpensive Offers

Oct 7 - Oct 14

-40%

~~$656~~

$395 per night

House ∙ 9 guests ∙ 4 bedrooms

House in Western Branch South with Hot Tub & Yard + Beautiful View

Western Branch South, Chesapeake, Virginia, United States

Details

Evolve

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Jul 14 - Jul 21

$185 per night

House ∙ 2 guests ∙ 3 bedrooms

Pleasant Vacation Home in Indian River

3.0

(3 ratings)

Indian River, Chesapeake, Virginia, United States

Details

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Mar 23 - Mar 30

-20%

~~$244~~

$195 per night

House ∙ 5 guests ∙ 2 bedrooms

Nice Vacation Home in Greenbrier West + Water View

Greenbrier West, Chesapeake, Virginia, United States

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Vacation rentals with Wi-Fi

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

Mar 23 - Mar 30

$331 per night

House ∙ 4 guests ∙ 2 bedrooms

House in Chesapeake with Yard & Pool

5.0

Outstanding (2 ratings)

Chesapeake, Virginia, United States

Internet

Details

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Mar 23 - Mar 30

$130 per night

House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Greenbrier West

4.6

Excellent (5 ratings)

Greenbrier West, Chesapeake, Virginia, United States

Internet

Details

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Oct 1 - Oct 8

-27%

~~$276~~

$203 per night

Condo ∙ 6 guests ∙ 1 bedroom

Condo in Indian River with Complimentary Parking

Indian River, Chesapeake, Virginia, United States

Internet

Details

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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.

Sep 30 - Oct 7

$96 per night

Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Culpepper Landing

Culpepper Landing, Chesapeake, Virginia, United States

Kitchen

Details

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Jul 14 - Jul 21

$129 per night

House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Western Branch North

Western Branch North, Chesapeake, Virginia, United States

Kitchen

Details

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Sep 30 - Oct 7

-29%

~~$271~~

$191 per night

Condo ∙ 4 guests ∙ 1 bedroom

Condo in Indian River with Indoor Pool

Indian River, Chesapeake, Virginia, United States

Kitchen

Details

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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.

Nov 11 - Nov 18

-30%

~~$225~~

$158 per night

Apartment ∙ 3 guests ∙ 1 bedroom

Apartment in Indian River with Indoor Pool + City View

Indian River, Chesapeake, Virginia, United States

Air conditioning

Details

Vrbo

View deal

Nov 11 - Nov 18

-30%

~~$225~~

$158 per night

Apartment ∙ 3 guests ∙ 1 bedroom

Apartment in Indian River with Indoor Pool + City View

Indian River, Chesapeake, Virginia, United States

Air conditioning

Details

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Mar 23 - Mar 30

$128 per night

House ∙ 12 guests ∙ 3 bedrooms

House in Indian River

Indian River, Chesapeake, Virginia, United States

Air conditioning

Details

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Popular Rental Amenities in Chesapeake

Pet-friendly (69)
Pool (286)
WiFi (599)
TV (570)
Air conditioning (566)
Kitchen (257)
Washing machine (291)
Parking (16)
Grill (147)
Microwave (504)
Fishing (10)
Dishwasher (112)

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 11, 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

Tue, 26 Sep

71°

66°

Wed, 27 Sep

69°

66°

Thu, 28 Sep

69°

66°

Fri, 29 Sep

80°

64°

Sat, 30 Sep

78°

68°

Sun, 1 Oct

75°

69°

Mon, 2 Oct

73°

68°

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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	629 homes
💳 Possible discounts	up to 56%
🌙 Nightly prices starting at	$66
⭐ Popular amenities	Pets allowed, Pool and Internet
🐾 Pet friendly homes	63 homes
🏊 Vacation rentals with pools	285 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 $66. If you’re interested in a house rental, the average price is $383 per night. A apartment rental Chesapeake will cost $183 per night on average.

How many vacation homes are available for booking in Chesapeake?

Currently there are 629 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 285 Hotel room and Condo options available for booking.

Are pets allowed in vacation rentals in Chesapeake?

Absolutely, there are 63 vacation rentals in Chesapeake that allow dogs , with an average nightly rate of $215.

We list offers from thousands of providers, including

House Rentals in Chesapeake

Choose the perfect vacation rental

Cozy Chesapeake Vacation Rentals Amidst History and Nature

Best Vacation Home Deals in Chesapeake

Top-Rated Rentals and Accommodations in Chesapeake

Recommended Vacation Rentals in Chesapeake

Budget-friendly Vacation Rentals in Chesapeake

Vacation rentals with Wi-Fi

Apartments and vacation rentals with a kitchen

Vacation rentals and apartments with air conditioning

Popular Rental Amenities in Chesapeake

7-Day Weather Forecast in Chesapeake

What to Eat in Chesapeake

Unique Local Art and Culture

Fun Activities for the Family

What to See and Do in Chesapeake

A Variety of Festivals

Information about vacation rentals in Chesapeake

Frequently Asked Questions

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

How many vacation homes are available for booking in Chesapeake?

What amenities are most popular for vacation homes in Chesapeake?

How many vacation rentals with pools are there in Chesapeake?

Are pets allowed in vacation rentals in Chesapeake?

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