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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 G$6,274 GYD 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
Guest suite in Virginia Beach
4.9 out of 5 average rating, 746 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.

Guest favorite
A bright kitchen is highlighted by light-colored cabinetry and natural wood flooring. The countertop displays a cutting board, and the sink is complemented by a stylish faucet. Large windows allow natural light to fill the space, enhancing the tile backsplash's subtle patterns.
Home in Norfolk
4.82 out of 5 average rating, 381 reviews

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.

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
5 out of 5 average rating, 103 reviews

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

Superhost
A corner of the bedroom features a comfortable armchair and a small side table next to it. Natural light enters through two windows, highlighting the polished hardwood floor. A vintage door leads to the front porch, adding charm to the space.
Vacation home in Portsmouth
4.74 out of 5 average rating, 168 reviews

Lovely 2-bedroom 1100 sq ft Apt with free parking

You will enjoy easy access to everything in downtown Portsmouth from this centrally located place. You are in a residential area two blocks from the heart of downtown Portsmouth, a half a mile to the Portsmouth Naval Hospital in the Historic Olde Towne district and a Starbucks one block away. The Virginia Beach ocean front is a half hour away by car. This is a historic building on the National Register of Historic Places. It consists of four apartments; one on the second floor is your Airbnb.

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
4.92 out of 5 average rating, 170 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!

Top guest favorite
Apartment in Chesapeake
4.99 out of 5 average rating, 186 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.

Top guest favorite
A spacious studio area is highlighted by a king-size bed with a white bedspread and decorative pillows. A cozy seating arrangement and dining table are seen, alongside a fireplace and wall-mounted TV. Soft lighting enters through the windows adorned with wooden blinds.
Guest suite in Virginia Beach
4.97 out of 5 average rating, 194 reviews

Quiet Suite with Private Entrance

Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

Top guest favorite
A house with a blue and white exterior is situated on the edge of the water, reflecting in the calm surface. Lily pads float nearby, while flags adorn the porch railing, indicating a welcoming environment. Greenery surrounds the area, enhancing the serene landscape.
Home in Moyock
4.94 out of 5 average rating, 399 reviews

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.

Top guest favorite
Home in Chesapeake
4.96 out of 5 average rating, 135 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!

Top 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
4.85 out of 5 average rating, 115 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!

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
4.9 out of 5 average rating, 102 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.

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
4.99 out of 5 average rating, 157 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

Popular amenities for Chesapeake pet-friendly home rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$24,470 GYDG$24,261 GYDG$25,725 GYDG$23,425 GYDG$24,470 GYDG$24,679 GYDG$25,725 GYDG$25,098 GYDG$22,588 GYDG$23,006 GYDG$24,261 GYDG$25,516 GYD
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

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