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Pet-friendly holiday 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

4.84 out of 5 average rating, 224 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

Guest favourite

Home

5 out of 5 average rating, 102 reviews

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

Guest favourite

Guest suite

4.98 out of 5 average rating, 136 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

4.86 out of 5 average rating, 122 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!

Home

4.88 out of 5 average rating, 107 reviews

Beach Hideaway 2 bdr/2bth- Pet friendly!

Great home for days at the beach and a fire pit at night! Beach access 1 1/2 blocks from the home. Heat/AC, dishwasher, w/d, and deck. Linens, bath towels, beach chairs, and beach towels are provided. Quiet family beach, bay water is calm- perfect for children. Large back yard for kids to run around, deck, and enclosed front porch. Close to Virginia Beach, Norfolk military bases and ODU, EVMS, NSU, Virginia Wesleyan, Hampton Univ. Approx 25 min from downtown Virginia Beach and W-burg.

Guest favourite

Home

4.9 out of 5 average rating, 125 reviews

4 BR | Pet Friendly | Fenced Yard | Firepit

Welcome to Norfolk! This is a large 3 story, 4 BR/3.5 BA house located just outside of the popular Ghent district in and walking distance to many breweries, restaurants & coffee shops! This is a fast growing area of town and for good reason, we’re so exited to host you! 15 min drive to Norfolk International Airport 12 min drive to Naval Base 8 min drive to Downtown/waterside district/freemason historic district 6 min drive to ODU campus 4 min drive to Virginia Zoo

Guest favourite

Home

4.84 out of 5 average rating, 343 reviews

Family Holiday House. Events and Beaches Nearby

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.

Guest favourite

Cottage

4.97 out of 5 average rating, 237 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.

Guest favourite

Townhouse

4.97 out of 5 average rating, 142 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.

Guest favourite

Home

4.92 out of 5 average rating, 137 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.

Guest favourite

Townhouse

4.81 out of 5 average rating, 191 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

Guest favourite

Cottage

4.95 out of 5 average rating, 365 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

Guest favourite

Home

4.96 out of 5 average rating, 128 reviews

Water Oaks at Chic's Beach

Guest favourite

Home

4.92 out of 5 average rating, 37 reviews

Cozy and Modern Beach House

Guest favourite

Home

4.96 out of 5 average rating, 105 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

Guest favourite

Home

4.92 out of 5 average rating, 183 reviews

@Whit’s End? Come in and Relax

Guest favourite

Home

4.86 out of 5 average rating, 111 reviews

Cozy Country Cottage

Guest favourite

Home

4.84 out of 5 average rating, 143 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

Guest favourite

Home

4.95 out of 5 average rating, 135 reviews

Family hideaway

Home

4.84 out of 5 average rating, 32 reviews

Cozy 3 BDRM home w/HUGE fenced-in yard near beach

Pet-friendly home rentals with a pool

Home

4.89 out of 5 average rating, 19 reviews

Upscale Ocean View, Heated Pool, Steps to Beach

Guest favourite

Home

5 out of 5 average rating, 37 reviews

Paint The Beach Pink! Full House | Gas Fire Pit

Guest favourite

Guest house

4.73 out of 5 average rating, 100 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

Guest favourite

Home

4.94 out of 5 average rating, 87 reviews

Gorgeous Vacation House

Guest favourite

Place to stay

4.93 out of 5 average rating, 76 reviews

North End Home with pool, beach & state park.

Home

4.67 out of 5 average rating, 73 reviews

Beach House with breathtaking sunsets

Guest favourite

Home

4.84 out of 5 average rating, 82 reviews

Perfect Getaway!

Guest favourite

Campsite

5 out of 5 average rating, 7 reviews

RV Lot (No RV) near all amenities

Private, pet-friendly home rentals

Home

4.8 out of 5 average rating, 25 reviews

New! Clean + Affordable + Central!

Home

4.88 out of 5 average rating, 52 reviews

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

Guest favourite

Bungalow

4.95 out of 5 average rating, 95 reviews

Private and Cozy Bungalow Loaded with Amenities

Flat

5 out of 5 average rating, 4 reviews

The Southern Magnolia | 2br/1bth Home

Guest favourite

Flat

4.97 out of 5 average rating, 184 reviews

Centrally Located Sleek Studio Apartment

Guest favourite

Home

4.92 out of 5 average rating, 13 reviews

Quiet & Private, Comfy Beds, Fire Pit, & Bikes

Guest favourite

Campervan/Motorhome

4.95 out of 5 average rating, 22 reviews

Chesapeake Retreat

Guest favourite

Home

5 out of 5 average rating, 38 reviews

An Emperor’s Nest

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

Total rentals
280 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
270 properties include access to wifi

Destinations to explore