
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.

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

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.

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

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.

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.

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!

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!

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!

R & R River House
Have a peace of mind when you rent this luxury condo with beautiful water views. Totally remodeled condo with high-end finishes. This home is perfect for a couple getaway or family for fun with the nearby city park (1 mi). The peaceful condo is located close to the Casino (4.5 mi), Downtown Portsmouth (7 mi), Waterside (7.6 mi), and Virginia Beach (25 mi). Be amazed with this nestled away condo in safe neighborhood.

3BR Mid-Century Modern Home • Near Airport
Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!
Popular amenities for Chesapeake house rentals
House rentals with a pool

Retreat with Pool, Walk to Beach

Artful Retreat with a Private Pool

Country Comfort Close to the Beaches

Gorgeous Vacation House

Bayfront Pool Retreat, Walk to Beach

Sunrise, North End Beach / Oceanfront Area

Ocean Pearl- Canal View and Minutes to the beach

Half house w/pool & new patio all to yourself
House rentals with free parking

3 bedroom private home a block from the beach!

Beautiful 3bdrm near beach, Wi-Fi & parking

10 min to Ocean View Beach: 20% Off Aug

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

Norfolk Beach Bungalow | Pet-Friendly + Deck

Walk to Beach! Fully Updated + Hot tub!

Play by the Bay 1 MIN TO WATER

Quiet 3/2 beautiful Chesapeake
Weekly house rentals

Southern Charm Warm and Welcome

Blessed and peaceful home

Private Beachfront Modern Villa: Outdoor Shower!

Spacious 3 Bedroom Home | Near many Shops & Dining

15 minutes to the beach bungalow

The Bird’s Nest

Simply Amazing in Chesapeake

Comfy House! The Perfect Getaway
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
- Corolla Beach
- Cape Charles Beachfront
- Buckroe Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Neptune's Park
- Currituck Club
- Currituck Beach Lighthouse
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Chrysler Museum of Art
- Nauticus
- Hampton University





