
House vacation rentals in Chesapeake
Find and book unique houses on Airbnb
Quick stats about house rentals in Chesapeake

Total vacation rentals
Explore 550 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

Verified guest reviews
Over 16,510 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

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

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

4.8 Average rating
Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Aerotheater
Top-rated house rentals in Chesapeake
Guests agree: these houses are highly rated for location, cleanliness, and more.

Mason Manor - Downtown Smithfield next to WCP
Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.
FamilyLocationPets

Hidden Gem.4/bedroom cozy home fenced in yard
Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles
LocationFamilySleep quality

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!
LocationValueAccess

2 Master Suites, Sleeps 6-8, King bed, 2.5 baths
Bring the whole family to this spacious home with plenty of room to relax. This is one side of a duplex featuring two master suites, each with its own en-suite bathroom, plus a convenient half bath downstairs. The home includes a king bed in one suite and two queen beds in the second, along with walk-in closets, washer and dryer, central heat and air, and a wonderful deck. Centrally located. Traveling with a larger group? Both sides of the duplex can be booked to accommodate up to 16 guests.
ValueLocationGetting around

Sportsman's Paradise ( Hunting & Fishing )
Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.
ValueLocationAmenities

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!
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Play by the Bay 1 MIN TO WATER
LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.
LocationValueView

Artful Retreat with a Private Pool
Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!
ValueLocationAccuracy

Perfect Getaway!
Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!
LocationValueLaundry

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. Bring your fishing poles!
ValueFamilyCondition

3 bedroom private home a block from the beach!
Relax with the whole family at this peaceful home. A block to the beach! 3 bedrooms and 2 bathrooms, with an outdoor shower and finished basement with extra living space. Outdoor patio with gas grill and patio furniture. All amenities included sheets, towels, cooking utensils, etc. Fast Wi-Fi throughout the home. Can sleep up to 8! Pets always welcome. All bedrooms are on main level no stairs required. Weekly and monthly discounted rates upon inquiry.
LocationValueBackyard

Cook's Country Escape - Cozy Retreat
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. It’s been a great rental with great ratings.
LocationFamilyCondition
Popular amenities for Chesapeake house rentals
House rentals with a pool

Ocean Pearl- Canal View and Minutes to the beach
FamilyValueHeating

Gorgeous Vacation House
FamilyValueLayout

4BD home w/ game room & pool near Langley & PTC!
LocationValueOutdoor spaces

Country Comfort Close to the Beaches
LocationValueAmenities

Designer Beach House | Pool, Hot Tub, Walk to Sand
LocationFamilyComfort

Half house w/pool & new patio all to yourself
LocationValueGetting around

The Great River Escape *Hot Tub!
ValueLocationComfort

Bayfront Pool Retreat, Walk to Beach
LocationFamilyGetting around
Weekly house rentals

Penny’s Palace 1 Bed/1 Bath Home
FamilyValueLayout

Beach Stay
LocationValueLaundry

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ
LocationFamilyGetting around

Beautiful 3bdrm near beach, Wi-Fi & parking
ValueFamilyCheck-in

2 Min Walk to Beach • Fenced Yard • Parking
FamilyValueBathroom

@Whit’s End? Come in and Relax
LocationValueCheckout

Cozy Retreat
LocationValueView

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
ValueLocationNearby
Private house rentals

Comfy House! The Perfect Getaway
ValueLocationQuiet

Quiet 3/2 beautiful Chesapeake
FamilyValueComfort

Cowbell Cottage
LocationValueLong stay

Spacious 3 Bedroom Home | Near many Shops & Dining
LocationFamilyIndoor spaces

Riverfront 3BR Retreat • Near Rivers Casino
ValueLocationCheck-in

The Bird’s Nest
FamilyLocationCondition

Blessed and peaceful home
ValueFamilyQuiet

Simply Amazing in Chesapeake
FamilyLocationCleanliness
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 419 | ﺩ.ﺇ 389 | ﺩ.ﺇ 422 | ﺩ.ﺇ 459 | ﺩ.ﺇ 485 | ﺩ.ﺇ 510 | ﺩ.ﺇ 466 | ﺩ.ﺇ 441 | ﺩ.ﺇ 397 | ﺩ.ﺇ 404 | ﺩ.ﺇ 419 | ﺩ.ﺇ 422 |
| 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 |
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- Chrysler Museum of Art
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Virginia Living History Museum
- Currituck Beach





