Pet-friendly holiday rentals in Pittsfield

4.97 out of 5 average rating, 112 reviews

A cozy room features a spacious bed with a plaid blanket, a woodstove positioned against a natural wood accent wall, and a rocking chair. Multiple windows allow natural light, highlighting the wooden ceiling and fir floor. A small dresser complements the room's rustic charm.

Cabin in Bethel

Firefly Cottage

Relax in this calm Nordic-style space. Rocking chairs on the porch overlook a pond, meadow, and spectacular seasonal fireflies. 140 woodland acres to explore with old (rough) logging trails with views, sheep and chickens you can feed. High ceilings, scenic window, woodstove, indoor waterless toilet, outdoor coldwater sink and outdoor private hot shower (when above freezing); available sauna at main house. 35-45 min to main ski areas. Most pets ok! Owner's home conveniently close but out of view.

PetsOutdoor spacesLocation

4.99 out of 5 average rating, 170 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

WalkabilityOutdoor spacesLong stay

4.99 out of 5 average rating, 266 reviews

A charming cabin stands beneath a clear blue sky, featuring a metal roof and large windows that provide ample natural light. Grassy areas surround the structure, with trees bordering the background, creating a serene rural setting.

Cabin in Royalton

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

WalkabilityOutdoor spacesHeating

4.93 out of 5 average rating, 115 reviews

A vibrant autumn landscape is visible, featuring a two-story green townhome bordered by a well-maintained lawn. Colorful foliage on nearby trees and surrounding hills creates a warm ambiance, highlighting the natural beauty of the area in this scenic outdoor view.

Townhouse in Killington

Topridge 3BR w Foliage Views & Private Hot Tub!

Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

Outdoor spacesComfortHiking

4.86 out of 5 average rating, 210 reviews

An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.

Chalet in Stockbridge

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

PetsWalkabilityDecor

4.99 out of 5 average rating, 112 reviews

An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.

Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

PetsOutdoor spacesCheckout

4.94 out of 5 average rating, 136 reviews

A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.

Cabin in Stockbridge

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

PetsOutdoor spacesCondition

4.94 out of 5 average rating, 279 reviews

A charming red house is set against a lush green backdrop. Large windows provide natural light and views of the surrounding trees. A wooden deck is featured at the front, leading to a beautifully maintained lawn, inviting outdoor activities.

Cabin in Hancock

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

Outdoor spacesPetsWi-Fi

4.94 out of 5 average rating, 308 reviews

A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.

Condo in Killington

Vermont Retreat, Dogs Welcome, Pool & Spa

Coffee on the patio. Mountains turning gold. Your dog already halfway down the trail. That’s summer and fall at The Woods. This spacious dog-friendly 2BR sleeps 6 and features a full kitchen, fireplace, private patio, and access to the indoor pool, hot tub, and spa. Minutes from Killington Bike Park, hiking, golf, and restaurants, it’s the perfect home base for Vermont adventures. Bring the crew. Bring the pup. This is the place guests rebook before checkout.

Outdoor spacesWalkabilityView

4.94 out of 5 average rating, 228 reviews

A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.

Chalet in Royalton

Scandinavian design Chalet hiking trail + hot tub

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

Outdoor spacesPetsCheck-in

4.85 out of 5 average rating, 256 reviews

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

PetsWalkabilityBathroom

4.93 out of 5 average rating, 152 reviews

A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.

Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

WalkabilityPetsCheck-in

Popular amenities for Pittsfield pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A cozy living room features a stone fireplace at its center, surrounded by natural wood paneling. Two red accent chairs are positioned beside a window, while a large gray sofa and green armchair offer ample seating. A coffee table rests in front, adorned with a textured blanket.

4.89 out of 5 average rating, 106 reviews

Brookview Lodge, Killington, VT

Outdoor spacesPetsIndoor spaces

A bright dining area is highlighted by a large wooden table, surrounded by black chairs. Natural light floods the space through multiple windows, accentuating the warm wooden beams above. A chandelier adds a touch of elegance, complementing the simple decor.

4.92 out of 5 average rating, 170 reviews

Atelier Killington, hottub and amazing location

PetsWalkabilityGetting around

4.94 out of 5 average rating, 125 reviews

A sunroom showcases high wooden ceilings with skylights, enhancing natural light. A comfortable seating area, set with a light-colored couch and side table, is positioned next to large windows offering views of the outdoors. A dining table, accompanied by four chairs, occupies one corner of the space.

Home in Rutland

Mountain Getaway Pet friendly

WalkabilityOutdoor spacesQuiet

4.78 out of 5 average rating, 276 reviews

Home in Randolph

Vermont Highland

Outdoor spacesWalkabilitySleep quality

4.98 out of 5 average rating, 175 reviews

Home in Mendon

New Firepit, Great Location, Dog Friendly, Kitchen

Outdoor spacesPetsCondition

4.98 out of 5 average rating, 179 reviews

A dining area is seen through an open doorway, featuring a wooden table surrounded by six chairs. Warm lighting is provided by a chandelier above, while a bowl of flowers centers the table. A patterned rug lies beneath, and cabinetry is visible in the background.

Home in Hartford

Charming, Cozy Cape

PetsWalkabilityLocation

4.93 out of 5 average rating, 252 reviews

A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.

Home in Roxbury

Captain Tom's Cabin - Secluded Vermont Getaway

Outdoor spacesPetsSkiing

4.96 out of 5 average rating, 177 reviews

An open-concept living area showcases rustic wooden beams and large windows, allowing natural light to fill the space. A dining table with wooden chairs is positioned near the kitchen, which features modern appliances and a cozy wood stove on a stone base.

Home in Granville

Epic Views of the Green Mountains

PetsOutdoor spacesCheck-in

Pet-friendly home rentals with a pool

4.88 out of 5 average rating, 307 reviews

The cozy living area features a pair of gray sofas positioned around a circular wooden coffee table. A fireplace is set against a green accent wall, accompanied by a flat-screen TV mounted above. Natural light filters through the large window adorned with blinds.

Townhouse in Killington

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Outdoor spacesPetsComfort

4.92 out of 5 average rating, 159 reviews

Apartment in Clarendon

Vermont Horse Farm

WalkabilityPetsBarbecue

4.91 out of 5 average rating, 1026 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

Outdoor spacesWalkabilitySleep quality

Superhost

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

Outdoor spacesPetsFamily

4.87 out of 5 average rating, 283 reviews

Superhost

Townhouse in Killington

Ski In/Out Spruce Glen C, AC, Sauna, Fireplace

PetsWalkabilityCheckout

4.84 out of 5 average rating, 112 reviews

4.94 out of 5 average rating, 486 reviews

A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.

Yurt in Randolph

Lower Yurt Stay on VT Homestead

PetsOutdoor spacesAccuracy

4.97 out of 5 average rating, 158 reviews

A spacious living area is highlighted by a stone-clad fireplace, surrounded by a large sectional sofa. Natural light filters through the draped windows, revealing a serene outdoor view. A rustic wooden shelf holds decorative items, and a stack of firewood is neatly arranged beside the fireplace.

Condo in Killington

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

PetsWalkabilityWi-Fi

Apartment in Williamstown

Cozy/Private, close to hospital, i-89

Outdoor spacesPetsAmenities

4.91 out of 5 average rating, 187 reviews

Private, pet-friendly home rentals

4.91 out of 5 average rating, 222 reviews

A charming two-story lake house apartment features a welcoming exterior with a covered porch adorned with hanging plants. Bright sunlit spaces are framed by large windows, and a grassy area is visible in the foreground, enhancing the outdoor ambiance.

Apartment in Salisbury

Doc's Lake House 1st floor, 2 bdrm full apartment

WalkabilityPetsHeating

A spa-like bathroom features a luxurious soaking tub beside a modern shower enclosed by glass. Multiple windows offer views of the wooded surroundings, while elegant wood accents complement the radiant floor heating. A stylish sink and cabinetry enhance the tranquility of the space.

4.93 out of 5 average rating, 56 reviews

Romantic Retreat, Hot Tub, near Killington Mtn

PetsOutdoor spacesFamily

A modern mountain house is set against a backdrop of tall trees under a clear blue sky. The structure features a sloped metal roof and a deck area with seating, while a picnic table is positioned on the grassy lawn, inviting outdoor gatherings.

4.84 out of 5 average rating, 88 reviews

Green Mountain/Killington Getaway

Outdoor spacesPetsComfort

4.95 out of 5 average rating, 81 reviews

Killington Chalet: Hot Tub, Fireplace, spacious 4b

PetsOutdoor spacesDecor

4.81 out of 5 average rating, 16 reviews

Mountain Home with Scenic Views

PetsOutdoor spacesHot tub

An aerial view showcases the expansive 10-acre estate surrounded by snow-covered mountains. The property features a serene, spring-fed pond reflecting the landscape, with a spacious home nestled near the water, offering an inviting retreat in a tranquil setting.

4.95 out of 5 average rating, 41 reviews

Mountain Top - Fresh Pond - Killington - Hot Tub

Outdoor spacesPetsSkiing

4.92 out of 5 average rating, 51 reviews

Chalet in Stockbridge

Private Mountain Sanctuary | 15 Min to Killington

WalkabilityPetsQuiet

A cozy outdoor fire pit is surrounded by natural stone, with a warm fire dancing in the center. The modern home is visible in the background, illuminated by string lights. The structure features a deck and tall windows, set against a wooded landscape at dusk.