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

Total holiday rentals
Explore 550 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $29 AUD per night before taxes and fees

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

Family-friendly holiday rentals
280 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 150 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
530 of Chesapeake holiday 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.

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

Charming Home by the Sea, a block from the beach!
Single family home steps from the beach. Parking for vehicles including garage. Outdoor/indoor dining areas. Gas grill & fully equipped kitchen with cooking essentials for stay at home meals. 3 bedrooms sleeps 8. Can accommodate additional guests for an up charge with air mattress and sheets provided. Pets welcome! Hardwood flooring and central AC/heat throughout. Walking distance to restaurants in the local area. 15 minutes to Norfolk Naval Station, 10 mins to Airport, 20 mins to VB boardwalk.

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!

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.

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!

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.

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 central heat and air conditioning, updated appliances, and carpeting. It’s centrally located and there is plenty of space for parking. This is a perfect place to recharge whether you’re visiting for work or a getaway!

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!

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!

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.

Historic Gem - Walk to Dining, Ferry & Waterfront
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!
Popular amenities for Chesapeake house rentals
House rentals with a pool

Ocean Pearl- Canal View and Minutes to the beach

Gorgeous Vacation House

Artful Retreat with a Private Pool

Country Comfort Close to the Beaches

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

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

The Great River Escape *Hot Tub!

Bayfront Pool Retreat, Walk to Beach
Weekly house rentals

Beach Stay

*Escape to the Tangerine Dream*

Family Holiday House. Events and Beaches Nearby

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

The Cozy Beach House

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

Mason Manor - Downtown Smithfield next to WCP

Cozy beach cottage! One block to the beach!
Private house rentals

Spacious 3 Bedroom Home | Near many Shops & Dining

Oasis at the Creek| Park, Family & Pet Friendly

The Bird’s Nest

Comfy House! The Perfect Getaway

Simply Amazing in Chesapeake

Blessed and peaceful home

Condo Near Portsmouth Naval on Webster Avenue

Riverfront 3BR Retreat • Near Rivers Casino
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $163 AUD | $151 AUD | $164 AUD | $179 AUD | $189 AUD | $199 AUD | $182 AUD | $171 AUD | $154 AUD | $157 AUD | $163 AUD | $164 AUD |
| 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 |
Destinations to explore
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- Rentals with pools Chesapeake
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- Family-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
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- Pet-friendly rentals Chesapeake
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- House rentals Virginia
- House rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Currituck Club
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Nauticus
- Town Point Park





