
House vacation rentals in Chesapeake
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Top-rated house rentals in Chesapeake
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THE POINT! Private waterfront Oasis!
Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Penny’s Palace 1 Bed/1 Bath Home
Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Quiet East Beach Bungalow, 1 block to beach!
Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

The Cozy Cottage Two Bedroom, King bed House
This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

Island Lotus Yoga & Spa
A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

Beautiful renovated 2Bed home!
Your next unforgettable beach getaway awaits with a stay at this charming and completely renovated 2-bedroom, 1-bathroom vacation rental centrally located in Norfolk. Spend sunny summer days at Ocean View Beach, or explore the sights and sounds of nearby First Landing State Park, followed by a quick bite to eat at a local seafood restaurant. At dusk, retreat back to 'Castaway Cottage' for a family BBQ on the propane grill and s'mores shared around the fire pit………………………………

Gorgeous Olde Towne historic home - modern updates
Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

Walk to Beach! Dogs OK, Backyard, Hot Tub, Pool
Welcome to Coral Cove in Corolla! Take it easy at this nearly new, well-appointed condo and relax under the stars in your own private hot tub! - 2bed, 2 bth, sleeps 6, 2 king beds + Queen sleeper sofa - Easy 8-10min walk to beach. - Dogs OK! (fee applies) - Beach Gear included w/wagon. - Linens and Beach towels included! - Single level with no steps to enter or leave. - Private Hot Tub - Private backyard with seating

Quilted Quarters by the Bay with Private Entrance
Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Ghent on the Corner: Cozy 3 bed 2.5 bath home
My cozy, 3 bed / 2.5 bath Norfolk home has a spacious 1st floor primary suite with a full bathroom, 2 bedrooms upstairs along with a 2nd full bathroom. No cleaning fee or checkout instructions. Pet-friendly! Free Wi-Fi, parking for 4 cars, grill & gazebo. Distances: CHKD - 5 min EVMS - 5 min Sentara Norfolk General - 5 min Waterside / Downtown - 10 min Ocean View - 20 min VB Oceanfront - 25 min

Cook's Country Escape - Cozy Retreat w/ Big Deck
Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home.
Popular amenities for Chesapeake house rentals
House rentals with a pool

York River Vacation Home

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

Gorgeous Vacation House

Stunning Views of Back Bay & Seconds to the Beach

Sunrise, North End Beach

MillerLight

THE OLD BEACON 4 I Beach Living

Spotless Treehouse | Pool | HotTub | Pickle | Pets
Weekly house rentals

Beach House~Hot Tub~3 Min to Sand~HUGE Kitchen

Southern Charm Warm and Welcome

Cozy Home Near Hospitals & Beach

The Main House

VB Town Center -4 Parking Spots! -Pets welcome!

Modern 2 bdrm home w/Firepit & bikes near Casino

Cornick Corner near "Rivers Casino"

Casa del Mar - Artful Cottage, 2-Min Walk to Beach
Private house rentals

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

The Mayfield

The Marilyn: Beautiful 2-Bdrm Home Near the Beach

R & R River House

Spacious 3 Bedroom Home | Near many Shops & Dining

Perfect for 2! Walk to Beach #2

Modern, Homely 3-bdrm|wParking|Centrally located.

Home Away From Home
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,906 GYD | G$22,369 GYD | G$22,996 GYD | G$23,624 GYD | G$24,251 GYD | G$25,087 GYD | G$26,550 GYD | G$25,087 GYD | G$22,578 GYD | G$22,996 GYD | G$23,833 GYD | G$24,042 GYD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about house rentals in Chesapeake

Total vacation rentals
Explore 580 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$4,181 GYD per night before taxes and fees

Verified guest reviews
Over 16,860 verified reviews to help you choose

Family-friendly vacation rentals
290 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 170 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wi-Fi availability
550 of Chesapeake vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- House rentals Virginia
- House rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- The NorVa
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Old Dominion University
- Currituck Beach Lighthouse
- First Landing Beach
- Virginia Living History Museum
- Chrysler Hall
- Currituck Club




