Pet-friendly vacation rentals in Williamsburg

4.98 out of 5 average rating, 116 reviews

The dining area features a wooden table surrounded by metal chairs, set near a sliding glass door leading to a deck. A centerpiece of purple flowers adds a touch of color. Modern light fixtures hang above, providing ample illumination.

Home in Charles City

Cap 2 Cap Cottage VA Capital Trail Charles City

Cap 2 Cap Cottage - Rural oasis awaits in a NEWLY RENOVATED COTTAGE on 6 acres. 52 mile Virginia Capital Trail (Jamestown - Richmond) is only 3/10 of a mile away.Primary suite w/ 1 King bed. Add'l bedroom w/ 1 Queen bed. 2 full baths. Great Wifi, Smart TV, fully equipped kitchen, private deck. Fantastic restaurant/brewery Indian Fields Tavern is 3 miles away. Perfect stay for cyclists ,history lovers or just unwinding. NO Smoking or parties. Colonial Williamsburg 24 miles, Richmond is 30 miles .

4.94 out of 5 average rating, 124 reviews

A modern house stands amidst a lush green landscape, featuring a combination of dark and light exterior finishes. Large windows allow natural light to flood in, with a stone path leading to the entryway. The surrounding area is filled with trees, enhancing the home's natural setting.

Home in Toano

Serenity Over 5 Acres: Historic Triangle Haven

*4500 sq.ft. fully furnished house w/ 4 bedrooms & loft. *Includes all the amenities you need to enjoy a peaceful stay. * Unwind w/ friends & family in this modern retreat nestled on 5 acres in the woods w/ waterfront view & a fire pit. *You’ll enjoy the secluded area & yet be close to the bustle & hustle of what Williamsburg can offer. *Only 15-20 minutes to major attractions such as, Colonial Williamsburg, Bush Gardens, Jamestown, Yorktown, outlet mall. *Master bathroom only has a bath tub

5 out of 5 average rating, 157 reviews

A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.

Farm stay in Smithfield

Cottage at Timberline Ranch in Smithfield Virginia

Relax on a private 30 acre horse farm. 8 miles from historic Smithfield, VA Spacious bedroom, double window with view of horse pastures. Room darkening drapes. Full length mirror with lighted makeup mirror, air purifier, ample sheets, blankets and pillows. Full kitchen like brand new and well stocked with necessities; cookware, dishes, paper products, spices. Large bathroom with ceiling heater, towel warmer, well stocked with towels and necessities. Washer and dryer, detergent supplied.

5 out of 5 average rating, 121 reviews

The historic house is framed by a white picket fence, accented by snow-covered grounds and trees. Its traditional architecture features a steep roof and dormer windows, with green shutters enhancing the classic look. The house appears inviting amidst a serene winter landscape.

Home in Williamsburg

History Art and Nature-110 Acres of Ancient Forest

WILLIAMSBURG AREA, SURRY, VA. Lightwood Forest is a beautiful historic house nestled in 110 acres of private woodland preserve. Surround yourself with history, antiques, art and nature, and over two miles of private hiking trails winding through the ancient forest. A true hands-on historical experience surrounded by nature. Lightwood Forest is in rural Surry County, on the south side of the James River, a short, free car ferry ride from Williamsburg and Jamestown, which runs 24/7, all year.

4.97 out of 5 average rating, 145 reviews

A red kayak rests at the edge of the serene reservoir, surrounded by trees that frame the waterway. The calm surface reflects the clear blue sky and soft ripples created by a gentle breeze, ensuring a tranquil outdoor experience.

Cottage in Lanexa

TooFine Lakehouse, pet friendly waterfront cottage

Cute & cozy (tiny) waterfront cottage nestled in a pine forest. Situated on an almost 3 acre point on the Diascund Reservoir this is THE perfect spot to get away from it all & still be in the middle of everything! Options abound - fishing from the dock, bird watching, canoeing, roasting marshmallows around the fire pit, swinging in the hammocks, napping on the screened in porch, grilling on the patio, reading in the loft, playing games (inside & out), or just chill & feel the vibe.

4.97 out of 5 average rating, 158 reviews

Two classic white Adirondack chairs are positioned on a grassy bank overlooking the calm water of the Rappahannock River, framed by gently swaying trees. The sky displays a soft transition of colors as the sun sets, creating a serene and inviting view.

Home in Locust Hill

Waterfront Cottage Getaway Views/Kayaks/Fire Pit

A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

4.97 out of 5 average rating, 255 reviews

A charming cottage is set against a backdrop of tall trees, showcasing a light-colored exterior. A welcoming front porch features comfortable seating and an American flag. The landscaped yard includes potted plants and a gravel pathway leading to the entrance.

Cottage in Gloucester

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Apartment in Williamsburg

The exterior of a cozy apartment is depicted, featuring a white facade with green shutters. A small porch is visible, accompanied by a sign indicating the apartment's name. Lush greenery and floral plants frame the entrance, while a gravel pathway leads to the door.

4.84 out of 5 average rating, 471 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

Cottage in Gloucester Courthouse

A historic sign for Glebefield, established in 1795, is positioned among mature trees. Bright yellow flowers add a pop of color in the foreground, contrasting with the earthy tones of the surrounding greenery, creating a serene and inviting atmosphere.

4.98 out of 5 average rating, 223 reviews

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

4.95 out of 5 average rating, 303 reviews

A cozy bedroom features a spacious bed adorned with a floral quilt. Nightstands with lamps sit on either side, offering soft lighting. Artwork in warm tones is displayed on the walls, complemented by a vintage mirror above the headboard. A comfortable seating area is visible in one corner.

Farm stay in Toano

Farm Stay - Guest Suite w/ Private Entrance

Ready to add some adventure (and a few new animal friends) to your Williamsburg trip? Stay at our cozy little homestead, where the coffee’s hot and the chickens are nosey. Watch amazing sunrises, sunsets and starry skies that’ll make you forget about city life. We also have goats and a couple of obnoxious geese to meet (if you want). Slow down, savor the countryside, and connect with our curious critters—only 15 minutes from Williamsburg.

4.96 out of 5 average rating, 114 reviews

A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.

Condo in Williamsburg

Walk to beach lovely 2/2 in "Kingsmill on James"

Lovely, quiet, large ground floor 2 bdrm 2 full bath condo in "Kingsmill on the James". Beautiful tree and Audubon bird sanctuaries, trails. Condo backs to greenbelt, within walking distance to Kingsmill's beach, spa, marina, Café. **please note condo is in "Kingsmill on the James", not Kingsmill Resort...there's spa and beach access, for dogs too, but not pool... to use pool and resort, please book directly through the resort

4.97 out of 5 average rating, 246 reviews

A single-story home is positioned on a grassy lot, surrounded by trees and bushes. A wooden staircase leads to the front porch, which is flanked by red shutters on the windows. The roof is gently pitched, and a clear blue sky with scattered clouds is visible above.

Home in Williamsburg

Casita on the Corner

The Casita is a cozy 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens-Water Country. The area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. There is a shopping center with a Grocery store and restaurants within walking distance from the property.

Popular amenities for Williamsburg pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly home rentals with a hot tub

4.96 out of 5 average rating, 81 reviews

A modern living area features a comfortable sofa adorned with decorative pillows and a cozy throw. A large dining table with natural wood tones is visible in the background, contrasting against a blue accent wall decorated with serene artwork. Ample lighting brightens the space.

Home in Willoughby

Stylish Beach House, Hot Tub, Pet Friendly

4.93 out of 5 average rating, 141 reviews

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

Apartment in Williamsburg

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.

4.85 out of 5 average rating, 171 reviews

Westgate Historic Williamsburg One Bedroom

4.96 out of 5 average rating, 96 reviews

A grand deck is viewed, featuring two white rocking chairs overlooking a vibrant sunset over the water. The sky is filled with shades of pink and orange, reflecting on the calm ocean surface. A dark wicker seating area is visible to the right.

Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

4.96 out of 5 average rating, 154 reviews

A private hot tub is situated on a wooden deck surrounded by trees, offering a serene retreat. Sunlight filters through the branches, creating dappled shadows on the tub's surface. A wooden wall adds a rustic touch, featuring a decorative crab motif.

Home in Irvington

Magical wooded cottage pool +priv hottub walk2town

4.89 out of 5 average rating, 148 reviews

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

Wickline Cabin on Moon Creek

5 out of 5 average rating, 21 reviews

A three-story beach house is presented, featuring a light blue exterior and multiple balconies. Lush greenery and floral landscaping are visible in the front yard. The structure is flanked by similar homes, contributing to a vibrant coastal community atmosphere.

Home in Buckroe Beach

Experience Luxury by the Bay! Beach House: Hampton

5 out of 5 average rating, 60 reviews

A spacious living room features large windows providing ample natural light and views of the surrounding landscape. A cozy sectional sofa is positioned nearby a wood stove. A streamlined table with decorative elements sits in the foreground, while dining chairs are visible in the background.

Cottage in Onemo

3 BR Bay Home w Private Dock & all the Amenities

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 272 reviews

Cottage in Bayview

Positano Villa

4.93 out of 5 average rating, 182 reviews

A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.

Condo in Williamsburg

Kingsmill 1bed/1ba on Golf Course 9th Fairway

4.84 out of 5 average rating, 61 reviews

An aerial view captures a spacious two-story house with a grey roof, bordered by manicured landscaping. A paved driveway leads to the front where a car is parked. Surrounding open space and trees create a serene, natural setting.

Home in Providence Forge

Beautiful country house with 5 bedrooms 4.5 baths

4.81 out of 5 average rating, 276 reviews

A wooden sign, oval in shape, displays the name 'The Blue Tango Beach House' with decorative starfish accents. Established in 2014, the sign is positioned against a textured blue backdrop, enhancing its coastal theme.

Home in Urbanna

Relax in Urbanna, @ The Blue Tango!

4.92 out of 5 average rating, 118 reviews

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

Home in Norfolk

Gorgeous Vacation House

5 out of 5 average rating, 44 reviews

A spacious living area is furnished with comfortable sofas and a coffee table, surrounded by natural light from the large windows. The open layout transitions into a modern kitchen with white cabinetry and stainless-steel appliances, enhancing the welcoming atmosphere for gatherings.

Home in Hartfield

Maddie's Place

4.99 out of 5 average rating, 123 reviews

The entrance to The Rosé Retreat features a welcoming porch with multiple chairs arranged for relaxation. Arching glass doors provide a view into the inviting interior, framed by decorative wreaths that add a touch of seasonal charm. Lush green foliage surrounds the exterior.

Home in Irvington

The Rosé Retreat: Fireplace-Screened Porch-RELAX

4.88 out of 5 average rating, 137 reviews

A vintage pull-behind camper sits by the water's edge, featuring a striking teal color that contrasts with the clear blue sky. Grassy surroundings provide a natural setting, inviting views of the serene shoreline and distant water.

Camper/RV in White Stone

“Old Smokey”A cozy, single bedroom, unique getaway

Pet-friendly house rentals

4.97 out of 5 average rating, 149 reviews

An aerial view captures the surrounding area, featuring a mix of residential homes and lush greenery with sandy beach access visible. The Chesapeake Bay Bridge-Tunnel stretches toward the horizon over calm waters, providing a scenic backdrop to the coastal neighborhood.

Home in Chic's Beach

Water Oaks at Chic's Beach

4.88 out of 5 average rating, 78 reviews

Home in Williamsburg

Williamsburg Retreat

4.92 out of 5 average rating, 215 reviews

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

Cozy beach cottage! One block to the beach!

5 out of 5 average rating, 135 reviews

A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.

Home in East Ocean View

Quiet East Beach Bungalow, 1 block to beach!

4.92 out of 5 average rating, 208 reviews

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

@Whit’s End? Come in and Relax

4.9 out of 5 average rating, 39 reviews

An aerial view captures a charming retreat located on a lush peninsula, surrounded by calm waters. Trees adorned with autumn foliage create a vibrant backdrop, while a grassy area offers seating. Sunlight reflects off the water, enhancing the serene atmosphere of the landscape.

Home in Topping

Waterfront Home - Dock, Kayaks, Fire Pit, Grill

5 out of 5 average rating, 18 reviews

A bright and airy living space showcases large windows framing views of lush greenery. A child is seen setting up a chess board on a central table, while comfortable seating options invite relaxation in the cozy atmosphere.

Home in Spring Grove

Analog Private Beach on 10 Acres