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Pet-friendly vacation rentals in Chesapeake

Find and book unique pet-friendly homes on Airbnb

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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Home in Williamsburg

4.84 out of 5 average rating, 210 reviews

Colonial Retreat

Enjoy a getaway in our 1940 Cape Cod home minutes from Colonial Williamsburg & Jamestown. Within biking distance to many attractions such as Williamsburg Winery, Jamestown Island & Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The house was refinished in 2021; you'll find an updated kitchen, smart TVs, large back patio & front porch. Please read the house rules before booking. No smoking. Need more space? Inquire about our other units

Home in Phoebus

4.85 out of 5 average rating, 181 reviews

Waterfront home with heated pool available!

This lovely, spacious waterfront home is full of things to do. It is the perfect get away! Enjoy views of the Hampton River while you relax in the heated salt water pool! You may have up to eight guests with our 4 bedroom 3 bath home. Additional guests are $30 per person and an air mattress can be provided upon request. Pets are welcome for $45 per pet, you must notify ahead of time. You may also have the pool heated during your entire stay for only $250. (DO NOT TOUCH THE POOL PUMP PLEASE)

Guest suite in Virginia Beach

4.98 out of 5 average rating, 129 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

Tiny home in East Ocean View

4.88 out of 5 average rating, 116 reviews

☼ Beach Bungalow- 5 min walk to beach | parking ☼

A cozy beach getaway is waiting for you! This adorable bungalow was completely renovated in 2021 and is fully equipped to make your beach stay a breeze! -5 min walk to the beach -8 min walk to a local coffee shop/brewery -25 min drive to Virginia Beach/boardwalk area -10 min drive to Norfolk Botanical Garden -20 min drive to the Zoo -10 min drive to Ikea / Norfolk Premium Outlets Explore the attractions of the area or bum it on the beach for your whole stay, this bungalow has it all!

Camper/RV in Hampton

4.99 out of 5 average rating, 212 reviews

M&M’s Airbnb

RELAX in our cozy and modern RV with dependable blazing fast internet or sit outside and enjoy the view of our 2 acre property on the edge of a wooded area. We are centrally located: 5-15 minutes to a golf course, the beach, walking paths, parks, playgrounds, museums, AMC 24, shopping malls, Historic Yorktown Battlefields, Mini Golf, Whole Foods & many restaurants. 24mins to Busch Gardens & Water Country, 35mins to Williamsburg & Jamestown, and 45-50min to VA Beach's Oceanfront.

Cabin in Cape Charles

4.95 out of 5 average rating, 139 reviews

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Home in Hampton

4.83 out of 5 average rating, 335 reviews

Beautiful Holiday House - close to Events/Beaches

Large comfy 5BR/3BA home in established neighborhood w/Roku TV & high speed internet! Near Buckroe Beach, Hampton Coliseum Event Center, NASA, Langley Air Base, Boo Williams Sports Arena and Newport News. Also near Virginia Beach, Williamsburg and Busch Gardens There are many parks for recreation. We have a large enclosed porch for lounging. The front entry has an easy wheelchair ramp. Restaurants galore and endless shopping. NEAR AIRPORTS in Newport News and Norfolk.

Townhouse in Virginia Beach

4.97 out of 5 average rating, 139 reviews

Entire Home - Close to Beach - Pet Friendly

Welcome to "The Crab Shack" located in Salt Marsh Point. This is our newly renovated home located just minutes from the oceanfront. Everything here is brand new, upscale, comfy and just waiting for you. Imagine relaxing on the front veranda in upscale patio furniture, offset umbrella, outdoor grill and privacy fence. Or take it inside to the professionally decorated beach themed setting, with everything brand new and waiting for you.

Bungalow in Buckroe Beach

4.9 out of 5 average rating, 224 reviews

Bungelow by The Beach 2BR 1BA CABLE-Hampton, VA

5 Minute walk to the BEACH! 2 Bedrooms queen bed, 1 Bathroom, Living Room, Fully Equipped Kitchen, Dining Room, We have also provided an Adjustable Port-a-Crib. Washer/Dryer, dishwasher, Central AC & Heat, Front Deck, Gas Grill, Wireless Internet, Microwave, Kuerig & Coffee Pot, Silverware, Dishes, Pots and Pans, Games, Smart TV in both Bedrooms and Living Room, AND MORE! Pet policy case by case, 1 dog only, under 35 lbs $35.00 fee.

Home in East Ocean View

4.92 out of 5 average rating, 120 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). EV Charger on premises. Up to 2 dogs allowed.

Townhouse in Chic's Beach

4.8 out of 5 average rating, 188 reviews

Chicks Beach Getaway large yard 500 yards to Beach

4 bedroom 3 bath duplex with a large yard, screened porch & large deck . This home is in the Chicks Beach area of Virginia Beach or Chesapeake Beaches. less than 500 yards walk to the beach. Nice back yard and screen porch. $100 for 1 pet and $75 for second. 2 pet max. PLEASE NOTE: Saturday check in and 7 night stay required starting June 4th 2024. Check out 10am checkin is 3:30pm 4 car max

Cottage in Virginia Beach

4.94 out of 5 average rating, 350 reviews

Seaglass Cottage

Brand new, sparkling clean, "Seaglass cottage" in a quiet, beach neighborhood! Two blocks from the exciting, artsy, "VIBE" district, with murals, marketplace and unique restaurants. Five blocks from the active, Virginia Beach Boardwalk with shopping, music and dining! Don't do the usual, hotel lobbies and crowds, come to a clean place that you can call your own!

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Popular amenities for Chesapeake pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Chic's Beach

4.96 out of 5 average rating, 127 reviews

Water Oaks at Chic's Beach

Home in East Ocean View

4.87 out of 5 average rating, 54 reviews

Walk to Beach! Large Fenced Yard, Dogs Welcome!

Home in Virginia Beach

4.92 out of 5 average rating, 37 reviews

Cozy and Modern Beach House

Home in Portsmouth

4.96 out of 5 average rating, 105 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

Home in East Ocean View

4.93 out of 5 average rating, 178 reviews

@Whit’s End? Come in and Relax

Home in Moyock

4.85 out of 5 average rating, 109 reviews

Cozy Country Cottage

Home in Norfolk

4.82 out of 5 average rating, 131 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

Home in Norfolk

4.86 out of 5 average rating, 28 reviews

Clean Comfy and Calm | Pets & Fast Wi-Fi

Pet-friendly home rentals with a pool

Cottage in Norfolk

4.97 out of 5 average rating, 231 reviews

Positano Villa

Home in Virginia Beach

5 out of 5 average rating, 30 reviews

Paint The Beach Pink! Full House | Gas Fire Pit

Home in Virginia Beach

4.92 out of 5 average rating, 13 reviews

Chic 2 En Suite Condo! Family & Pet Friendly

Home in Norfolk

4.95 out of 5 average rating, 80 reviews

Gorgeous Vacation House

Place to stay in Virginia Beach

4.93 out of 5 average rating, 76 reviews

North End Home with pool, beach & state park.

Home in Suffolk

4.83 out of 5 average rating, 78 reviews

Perfect Getaway!

Camper/RV in Sandbridge

4.94 out of 5 average rating, 17 reviews

RV on lot in private community

Condo in Williamsburg

4.96 out of 5 average rating, 115 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

Private, pet-friendly home rentals

Townhouse in Virginia Beach

4.93 out of 5 average rating, 160 reviews

Charming 3 BR / 3.5 BA with a Private Backyard

Home in Virginia Beach

4.88 out of 5 average rating, 51 reviews

3 King Beds & Dogs OK! VB Vibe District! Spacious!

Home in Corolla

4.82 out of 5 average rating, 22 reviews

06 BL Beach Therapy! Ocean Retreat!

Bungalow in Chesapeake

4.95 out of 5 average rating, 91 reviews

Private and Cozy Bungalow Loaded with Amenities

Home in Virginia Beach

4.87 out of 5 average rating, 100 reviews

The Happy Place-Quiet, North End 1 block to ocean!

Rental unit in Newport News

4.97 out of 5 average rating, 175 reviews

Centrally Located Sleek Studio Apartment

Home in Virginia Beach

4.71 out of 5 average rating, 7 reviews

Charming 3 BR Beach Cottage 1 Blk from Beach

Guesthouse in Suffolk

4.86 out of 5 average rating, 36 reviews

Lakeside Retreat

Quick stats about vacation rentals that are pet-friendly in Chesapeake

Total rentals
300 properties
Total number of reviews
10K reviews
Family-friendly rentals
170 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wifi availability
290 properties include access to wifi

Destinations to explore