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

Total holiday rentals
Explore 580 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 16,600 verified reviews to help you choose

Family-friendly holiday rentals
300 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wifi availability
550 of Chesapeake holiday rentals include wifi 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 Cinema Cafe-Greenbrier Mall
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

Dog-Friendly Norfolk Cottage Near Ocean View Beach
🏡 Cozy 3BR cottage sleeping up to 6 guests 🐶 Dog-friendly with pre-approval and fully fenced backyard 🌊 Only minutes from Ocean View beaches 🚗 Ample driveway parking for multiple vehicles 🍽️ Fully stocked kitchen for easy meals at home 📺 Smart TV & high-speed Wi-Fi included 🧺 In-home washer and dryer for added convenience 🌳 Quiet residential neighborhood near local attractions ⚓ Close to Naval Station Norfolk and Little Creek Base 🎨 Easy access to downtown Norfolk, Ghent, and Waterside

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!

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!

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.

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.

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.

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!

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!

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.

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!
Popular amenities for house rentals in Chesapeake
House rentals with a pool

Nautical Cottage

Retreat with Pool, Walk to Beach

The White Lotus - Oceanview Retreat + Wild Horses

Country Comfort Close to the Beaches

Gorgeous Vacation House

Bayfront Pool Retreat, Walk to Beach

Sunrise, North End Beach / Oceanfront Area

Farmhouse Retreat-POOL, Sauna, 10 min to BEACH
Weekly house rentals

*Escape to the Tangerine Dream*

Spacious 3 Bedroom Home | Near many Shops & Dining

The Bird’s Nest

Beach Bungalow • Navy Base • Quiet St • Dogs OK

Simply Amazing in Chesapeake

Comfy House! The Perfect Getaway

Quiet 3/2 beautiful Chesapeake

Cowbell Cottage
Private house rentals

Southern Charm Warm and Welcome

Blessed and peaceful home

R & R River House

Modern Comfort Minutes from Waterside & Downtown

Cozy Modern Retreat, Peaceful Stay Near Everything

Bayfront backyard with a dock, 3BR, Dogs Welcome!

Contemporary 5 BR, 4BA, Over 3500 SF Water Front

Historic Haven
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £85 | £79 | £86 | £84 | £87 | £90 | £95 | £90 | £81 | £82 | £85 | £86 |
| 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 lake access Chesapeake
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- Rentals with beach access Chesapeake
- Beach house rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with pools Chesapeake
- Family-friendly rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Cottage rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a firepit Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with breakfast Chesapeake
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- Waterfront rentals Chesapeake
- House rentals Virginia
- House rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- The Mariners' Museum
- Nauticus
- Town Point Park





