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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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A charming Cape Cod home with a spacious front porch is surrounded by lush greenery and colorful flowers. The sloping roof features three dormer windows, while the well-maintained lawn provides an inviting entryway. The porch is equipped with seating and decorative accents.

Home in Williamsburg

4.84 out of 5 average rating, 239 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

A charming beach house is presented, featuring a simple white exterior and a well-maintained landscape. The entryway is framed by two small trees, with a pathway leading to a front door. A wooden fence encloses the yard, enhancing the inviting and peaceful ambiance.

Home in Virginia Beach

4.87 out of 5 average rating, 101 reviews

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

Nicest area in VA Beach & 5 minute walk to the beach! Enjoy a private, peaceful, vintage beach house and fully fenced yard in exclusive North End's quiet family neighborhood! Away from the crowds w/ easy access to everything. Great for surfing, swimming, walking, biking (1st State Landing park nearby), kayaking, fishing, dreaming, or reading. Cul-de-sac location. Detached house with dog-friendly yard! Comes w/ sheets & towels, 3 bikes, surfboard, beach chairs, buggy & umbrella. Equipped kitchen.

A classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

Home in Cape Charles

4.95 out of 5 average rating, 142 reviews

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

Top guest favorite

A circular fire pit is surrounded by stone blocks, with logs burning brightly in the center. Smoke gently rises into the air, and the area is bordered by grass and a quiet wooded backdrop.

4.99 out of 5 average rating, 103 reviews

Surry Homeplace

Located a few miles from the ferry to Williamsburg, and one mile from Chippokes State Park, this home has the feel of camping with all the amenities of home! Inside you will find washer and dryer, wifi (this is dish wifi - Zoom will not work and sometimes it is spotty), two full bathrooms, and a fully stocked kitchen. Outside offers a fire pit, a charcoal grill, a fenced area for pets / limit 2 (30 pound max dog, NO CATS ) and plenty of room for parking. Smoking is NOT allowed in the house.

A three-story house features a light gray exterior with a welcoming yellow front door. Flanking the entrance are neatly trimmed shrubs and small trees, complementing the spacious front porch. The surrounding area includes well-maintained neighboring houses and a glimpse of a fenced backyard.

Home in Norfolk

4.9 out of 5 average rating, 133 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

A spacious home is depicted with a welcoming front porch featuring a gentle ramp for accessibility. Lush greenery surrounds the exterior, and the peaceful atmosphere is enhanced by the colorful sunset sky. The house showcases a combination of brick and siding with large windows.

Home in Hampton

4.83 out of 5 average rating, 357 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.

Top guest favorite

An airy living space features a comfortable pullout couch adorned with decorative pillows. A mounted television is positioned above a wooden entertainment unit. The open kitchen area showcases white cabinetry and appliances, while a staircase leads to the upper level. Natural light enters through multiple windows.

Bungalow in Chesapeake

4.95 out of 5 average rating, 102 reviews

Private and Cozy Bungalow Loaded with Amenities

This 650 sqft 2 story house is very cozy for a couple. There is a king size bed in the bedroom, with space for additional guests on the pullout couch downstairs. The neighbors are all very friendly! The home is fenced in with available street parking. There is a yard with a fire pit and chairs as well as a back porch to enjoy some time outside, weather permitting. Whether you are vacationing or working in the area you can enjoy this cute little home away from home.

Top guest favorite

A spacious living area features a large, L-shaped gray sectional sofa adorned with decorative pillows. Two side tables with lamps flank the sofa, while a central coffee table holds a decorative tray. Coastal-themed artwork and a shelf with accents are visible above, enhancing the beach-inspired decor.

Townhouse in Virginia Beach

4.97 out of 5 average rating, 147 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.

A peaceful bedroom features a spacious bed with white linens and a decorative orange pillow. On either side of the bed, glass lamps provide soft lighting. A piece of artwork depicting natural elements hangs above the headboard, enhancing the serene ambiance.

Cottage in Cape Charles

4.8 out of 5 average rating, 111 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

A two-story duplex is depicted, featuring a distinctive star accent on the upper level. A path leads towards the entrance, with a lawn and patio area visible. Soft outdoor lighting casts a welcoming glow on the property, emphasizing its inviting facade.

Townhouse in Chic's Beach

4.8 out of 5 average rating, 200 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

A cozy living area features a striped sofa and two light armchairs, arranged around a soft, plush area rug. Natural light enters through two windows, and a mounted television is placed on the wall. A dining area is visible in the background, adorned with a simple floral centerpiece.

Home in East Ocean View

4.91 out of 5 average rating, 165 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.

The front porch features two wooden rocking chairs positioned beside a welcoming doormat. A bright turquoise door adds a pop of color, while a stylish wall sconce provides illumination. The porch offers a comfortable spot to relax and enjoy the peaceful surroundings.

Townhouse in Cape Charles

4.93 out of 5 average rating, 139 reviews

Cozy retreat 2Bedroom/2Bath, 3 Blocks to Beach

Welcome to Peach Haven II! Renovated in 2021, this pet-friendly duplex in Cape Charles’ historic district sleeps 5. One block from a park with playground and tennis/pickleball courts, and 3 blocks from the beach. Features 1 bedroom (queen bed) and a 2nd with a custom full-size bunkbed. Stocked for comfort. Ask about renting the other side for more space!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Chesapeake pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly home rentals with a pool

Top guest favorite

A private saltwater pool is depicted, surrounded by a spacious patio area. The pool's clear blue water is inviting, with a ladder providing easy access. Lush greenery and a white fence frame the background, enhancing the serene ambiance near the Chesapeake Bay.

Cottage in Norfolk

4.97 out of 5 average rating, 244 reviews

Positano Villa

An aerial view captures the upscale oceanview retreat nestled among other coastal homes. A clear pathway leads from the property to the beach access point, while the ocean waves are visible in the background, providing a sense of proximity to the shoreline.

Home in Corolla

4.92 out of 5 average rating, 24 reviews

LUX Oceanview•Heated Pool•2-Min Walk to Beach

Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.

Home in Portsmouth

4.94 out of 5 average rating, 109 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.

Apartment in Williamsburg

4.85 out of 5 average rating, 169 reviews

Westgate Historic Williamsburg One Bedroom

A spacious dining area is highlighted by a long table surrounded by six turquoise chairs and a white cushioned chair at one end. A vase with fresh flowers is centered on the table. The adjoining kitchen features modern appliances and an open design, allowing for light to fill the space.

Home in Sandbridge

4.95 out of 5 average rating, 20 reviews

Beach Dreams Sandbridge

The pool area is showcased with a clear blue water feature and adjacent Jacuzzi. Surrounding lounge furniture and a nearby seating arrangement provide space for relaxation. The backdrop features a low, stone wall and buildings with a warm color palette, enhancing the community atmosphere.

Condo in Sandbridge

4.87 out of 5 average rating, 234 reviews

Ocean Escape

Home in Virginia Beach

4.86 out of 5 average rating, 133 reviews

Beach Home, Upscale Croatan Resort + Private Pool

The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.

Condo in Williamsburg

4.95 out of 5 average rating, 124 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

Pet-friendly home rentals with a hot tub

A charming blue beach house features a multi-level design with large windows that invite natural light. A spacious deck offers unobstructed views of the surrounding sandy landscape. Steps lead up to the entrance, enhancing accessibility to the home. Wild grasses frame the property.

Cottage in Corolla

4.88 out of 5 average rating, 147 reviews

Horses-Views-Dog Friendly-4WD Area

A multi-level beach house features a light blue exterior with white trim and spacious balconies. The front porch is accessed by a set of wooden steps, leading to the main entrance. A two-car garage is visible, surrounded by well-maintained landscaping.

Home in Corolla

4.92 out of 5 average rating, 12 reviews

Sound View! Dogs OK! Pool&Spa, Sound&Beach Access

A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.

Home in Cape Charles

4.75 out of 5 average rating, 4 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

A two-story beach house is situated within a landscaped area, featuring a blend of pastel colored exteriors. A large, paved driveway leads to the home, framed by well-maintained greenery and blooming flowers. Balconies extend from the upper level, enhancing outdoor living space.

Townhouse in Corolla

4.87 out of 5 average rating, 31 reviews

4 bedroom T/H, Hot tub, short walk to beach

Top guest favorite

An open floor plan kitchen is highlighted with stone countertops and stainless steel appliances. Natural light enters through large sliding doors, connecting indoor and outdoor areas. Stylish seating is arranged in the living space, featuring a cozy chair and decorative elements on the walls.

Home in Corolla

4.99 out of 5 average rating, 84 reviews

Coral Cove- Backyard-Hot Tub-Walk to beach-Dogs ok

A charming log cabin features a front porch with a wooden railing and seating area. Surrounding the cabin are landscaped flower beds, tall trees, and a well-kept lawn. The cabin's rustic design is complemented by its natural setting, offering a peaceful view of the waterfront.

Cabin in Smithfield

4.89 out of 5 average rating, 142 reviews

Wickline Cabin on Moon Creek

A cozy living area is furnished with two light blue sofas and a light-colored area rug. A ceiling fan hangs above, providing air circulation. In the background, a dining area with a wooden table and blue chairs is visible through an arched entryway, framed by bright natural light from window blinds.

Cottage in Norfolk

4.91 out of 5 average rating, 111 reviews

Cozy Cottage - NEW hot tub, dogs OK, fenced yard

A two-story blue beach house is showcased with white railings and large windows. A spacious porch with chairs is visible, and a large umbrella provides shade. A vibrant red star adorns the house's front. An accessible driveway leads to a vehicle parked beside the entrance.

Home in Corolla

4.89 out of 5 average rating, 53 reviews

7 Bedroom | Corolla Light Resort | Private Pool &

Pet-friendly house rentals

A spacious living area is shown, featuring hardwood floors and an open layout. Comfortable seating is arranged around a coffee table, with a stylish ceiling fan overhead. The kitchen is partially visible in the background, with wood cabinetry and modern appliances. A dining area is accessible to the left.

Home in East Ocean View

4.88 out of 5 average rating, 60 reviews

Walk to Beach! Large Fenced Yard, Dogs Welcome!

A cozy living space features a green armchair with a patterned cushion, along with a small dining table and four chairs. The kitchen area is visible, showcasing wooden cabinetry and modern appliances. Natural light floods in through blinds on the windows, enhancing the inviting atmosphere.

Home in Virginia Beach

4.93 out of 5 average rating, 44 reviews

Cozy and Modern Beach House

The exterior of a charming house is visible, featuring a light-colored facade and a green roof. A welcoming front porch with a swing is seen, surrounded by a grassy yard and small shrubs. The neighboring houses are also present, featuring a mix of colors and styles.

Home in Williamsburg

4.84 out of 5 average rating, 80 reviews

2 BR Family & Pet Friendly House - Williamsburg

A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.

Home in East Ocean View

4.92 out of 5 average rating, 189 reviews

@Whit’s End? Come in and Relax

The covered porch features a seating area with two white chairs and a small table, surrounded by hanging flower baskets. The front door is framed by large windows, allowing natural light into the space. Lush trees are visible in the background.

4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

The exterior of the home features a charming stucco façade with turquoise accents and a terracotta tile roof. The front door is framed by arched windows, creating a welcoming entry. Lush greenery surrounds the property, enhancing its inviting character.

Home in Norfolk

4.85 out of 5 average rating, 156 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

A dining area is set with a round table surrounded by eight upholstered chairs. The walls are painted in a calming blue, and large windows allow natural light to fill the space. In the background, a kitchen can be seen, featuring a modern layout.

Home in Williamsburg

4.86 out of 5 average rating, 257 reviews

Bamboo Bungalo Duplex Near Busch Gardens

A charming two-story house from 1845 is showcased with a light-colored exterior. A covered porch extends along the front, featuring steps leading up to the entrance. Lush greenery surrounds the property, while a partly cloudy sky adds a serene backdrop.

Home in Williamsburg

4.79 out of 5 average rating, 108 reviews

Historic Capitol Landing 3BR/2Ba home

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

Total rentals
280 properties
Total number of reviews
9.4K reviews
Family-friendly rentals
160 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