
Pet-friendly vacation rentals in Chesapeake
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Chesapeake

Total vacation rentals
Explore 280 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 11,140 verified reviews to help you choose

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

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wi-Fi availability
270 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 Aerotheater
Top-rated pet-friendly home rentals in Chesapeake
Guests agree: these pet-friendly homes 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
5.0 out of 5 average rating, 114 reviews
Peaceful beach @Courtyard Cottage Pets Allowed
Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.
4.98 out of 5 average rating, 316 reviews
Quiet Neighborhood 7 Miles From the Beaches
Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.
4.9 out of 5 average rating, 763 reviews
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!
4.93 out of 5 average rating, 176 reviews
Modern Luxury Peace & Quiet.
Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.
4.98 out of 5 average rating, 192 reviews
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!
4.95 out of 5 average rating, 139 reviews
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!
4.85 out of 5 average rating, 117 reviews
Villa Positano
This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.
4.96 out of 5 average rating, 303 reviews
Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ
Escape to our charming Airbnb, just steps from the beach! Perfect for groups up to 8, our home offers ultra-fast 1Gbps fiber internet, a dedicated workspace, and delightful amenities including a SCA-approved coffee maker, a grinder, and fun games like a giant Connect 4 and Foosball. Enjoy the outdoors with our two patios and a BBQ grill. With numerous local restaurants nearby, it’s the ideal getaway for both relaxation and adventure.
4.91 out of 5 average rating, 115 reviews
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
4.99 out of 5 average rating, 164 reviews
Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. NOTE: Pool is open from Memorial Day to Labor Day. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee.
4.94 out of 5 average rating, 685 reviews
Cozy beach cottage! One block to the beach!
Beach cottage! Dogs sleep for free! One block to the beach. 3 bedroom. 1 bath. 1 king, 1 queen and 2 twin beds. Large deck with outdoor seating and grill! One block from Karla’s Beach House (brunch and lunch). One block from Jessy’s Taqueria. About a mile from Cova Brewing Co. (Brewery and Coffee) and East Beach Farmer’s Market (Saturdays from 9-12). Up to 2 dogs allowed.
4.94 out of 5 average rating, 283 reviewsPopular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
4.97 out of 5 average rating, 145 reviews
@Whit’s End? Come in and Relax
4.91 out of 5 average rating, 235 reviews
Sportsman's Paradise ( Hunting & Fishing )
4.94 out of 5 average rating, 402 reviews
Beach Ranch House Sleeps 9 and Pet Friendly
4.91 out of 5 average rating, 523 reviews
Norfolk Beach Bungalow | Pet-Friendly + Deck
4.87 out of 5 average rating, 109 reviews
Beach Hideaway 2 bdr/2bth- Pet friendly!
4.86 out of 5 average rating, 173 reviews
Water Oaks at Chic's Beach
4.97 out of 5 average rating, 172 reviews
Family hideaway
4.94 out of 5 average rating, 178 reviewsPet-friendly home rentals with a pool

Gorgeous Vacation House
4.9 out of 5 average rating, 145 reviews
4BD home w/ game room & pool near Langley & PTC!
4.87 out of 5 average rating, 141 reviews
Ocean Escape
4.86 out of 5 average rating, 279 reviews
Waterfront Oasis: Fishing Pier, Pool, Beach Access
4.71 out of 5 average rating, 14 reviews
Key Lime Cabana at Surfside
4.97 out of 5 average rating, 68 reviews
3 Bdrm home with Hot Tub
4.67 out of 5 average rating, 52 reviews
The Sportman's Lodge
4.92 out of 5 average rating, 72 reviews
Just steps from the beach! 8bdrm, 6bath
4.99 out of 5 average rating, 94 reviewsPrivate, pet-friendly home rentals

Chic's Beach Rental and Fishing
4.98 out of 5 average rating, 258 reviews
Lovely Ocean View Cottage
4.97 out of 5 average rating, 400 reviews
Enjoy your little slice of heaven in Chics Beach!
4.94 out of 5 average rating, 279 reviews
Beachfront Getaway, Pet Friendly, Mermaid Suite
4.99 out of 5 average rating, 112 reviews
Quiet 3/2 beautiful Chesapeake
4.94 out of 5 average rating, 69 reviews
The Bird’s Nest
4.91 out of 5 average rating, 66 reviews
Oasis at the Creek| Park, Family & Pet Friendly
4.9 out of 5 average rating, 73 reviews
Spacious 3 Bedroom Home | Near many Shops & Dining
4.93 out of 5 average rating, 71 reviewsWhen is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €102 | €101 | €107 | €107 | €110 | €121 | €107 | €104 | €94 | €96 | €101 | €106 |
| 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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- Pet-friendly rentals Virginia
- Pet-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Carova Beach
- Cape Charles Beachfront
- 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
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University





