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.

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Top guest favorite
A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.
Home in Portsmouth

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
Top guest favorite
A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.
Cottage in Norfolk

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
Guest favorite
Guest suite in Virginia Beach

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
Guest favorite
An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.
Home in Portsmouth

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
Guest favorite
Apartment in Chesapeake

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
Guest favorite
Home in Chesapeake

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
Guest favorite
A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.
Home in Suffolk

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
Top guest favorite
Cottage in Norfolk

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
Guest favorite
The living room features a welcoming layout with plush blue couches and two light-colored round ottomans. A ceiling fan hangs above, and natural light streams in through multiple windows. The front door is painted in a vibrant teal, adding a cheerful touch.
Home in Norfolk

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
Top guest favorite
A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.
Home in Norfolk

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
Guest favorite
The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.
Guest suite in Chesapeake

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
Guest favorite
Home in Norfolk

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 reviews

Popular amenities for Chesapeake pet-friendly home rentals

When is the best time to visit Chesapeake?

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