Pet-friendly holiday rentals in Pittsfield

Guest suite in Lake Bomoseen

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

4.97 out of 5 average rating, 242 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

4.93 out of 5 average rating, 300 reviews

Townhouse in Killington

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space so you can focus on business when not on the slopes

4.93 out of 5 average rating, 145 reviews

Home in Killington

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

4.95 out of 5 average rating, 415 reviews

The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.

Farm stay in Salisbury

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Superhost

The exterior of a contemporary timber home is visible, featuring a sloped green metal roof and warm wood siding. Surrounding snow-covered ground reflects nearby evergreen trees. The property is situated on a spacious lot, offering a serene winter landscape.

Townhouse in Killington

4.84 out of 5 average rating, 109 reviews

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC

Come and enjoy the largest private trailside property in Killington (almost 4 acres), with more convenience and value than large house rentals and more privacy than condo villages. The direct ski on/off is the easiest you'll find in Killington. Quiet and serene, the mature New England Evergreens and gentle mountain stream are a tranquil relief. An ideal ski in ski out or any season vacation getaway. Great Eastern is the longest green run in the East. Welcome to Spruce Glen!

4.94 out of 5 average rating, 267 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.

4.97 out of 5 average rating, 221 reviews

A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.

Home in Rochester

The Guest House at Sky Hollow

This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

4.84 out of 5 average rating, 240 reviews

A vibrant bedroom features floral wallpaper and peach curtains. A spacious bed adorned with colorful pillows is positioned against one wall. Two windows allow natural light to fill the room. The pink door adds a cheerful touch, while a cozy chair is placed nearby.

Flat in Rutland

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

4.95 out of 5 average rating, 161 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

4.85 out of 5 average rating, 246 reviews

A welcoming living area features a large fieldstone fireplace, with a soft couch and several armchairs arranged for comfort. A coffee table sits in the center of the space. Above, warm lighting illuminates an adjacent dining area, enhancing the cozy atmosphere.

Home in Pittsfield

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.

4.79 out of 5 average rating, 115 reviews

An A-Frame chalet is partially covered in snow, surrounded by a winter landscape. Snowmobiles are parked in front, with a vehicle also snow-blanketed. The wooden balcony and large windows suggest a cozy interior, while the sloped roof reflects the seasonal setting.

Chalet in Stockbridge

"Swiss Charm"- A Beautiful Riverfront Chalet

Nestled comfortably on the banks of the Tweed River just 9 miles North of the Killington Access Road just off Rt. 100, "The Skiers Highway" with Direct Access to VAST Trails. A 2BR 1 BA A-Frame Chalet is the perfect Pet Friendly weekend getaway. Quaintly decorated and well stocked...This is truly a "Home Away From Home".

4.93 out of 5 average rating, 150 reviews

A rustic wooden guesthouse is set against a backdrop of snow-covered ground and bare trees. The structure features large windows framed in dark wood, creating a contrast with the surrounding white landscape. Mountains are faintly visible in the distance.

Guest house in Strafford

Spacious Country Guesthouse

Strafford is a picturesque Vermont village. Our light-filled guesthouse, a former art studio in our backyard is an easy walk to the general store, a quick drive to historic sites and many local hiking trails. It has a loft bedroom and long-range river valley views.

Popular amenities for Pittsfield pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 227 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

4.97 out of 5 average rating, 183 reviews

The exterior of the cottage displays a modern design with light gray siding and a vibrant purple door. A small porch offers space to relax, while surrounding trees enhance the peaceful environment. A pathway is visible, leading to the entrance of the home.

Home in Middlebury

Purple Door Cottage in the heart of Middlebury!

4.97 out of 5 average rating, 150 reviews

A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.

Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

4.94 out of 5 average rating, 136 reviews

A vintage gas station building features a white exterior with red lettering spelling 'TEXACO.' Large glass windows line the front, showcasing a clear view of the interior. The American flag is displayed prominently, and a tree-lined background adds a touch of greenery.

Home in Castleton

Cozy Contemporary Downtown Texaco

4.99 out of 5 average rating, 161 reviews

A newly renovated house is nestled among tall trees, surrounded by lush greenery. The structure features multiple windows reflecting sunlight, with a wooden deck visible in the foreground, leading to a serene setting that invites outdoor relaxation.

Home in Woodstock

Beautiful Woodstock Home-Perfect for entertaining

4.96 out of 5 average rating, 178 reviews

Large glass doors frame a stunning mountain view, showcasing the surrounding landscape. A spacious deck with outdoor seating is visible. Inside, a wooden dining table with several chairs is positioned nearby, illuminated by pendant lighting, and a spiral staircase offers access to the upper level.

Home in Waitsfield

Mid century modern gem with views of Sugarbush

4.84 out of 5 average rating, 317 reviews

A serene outdoor setting features a two-story house surrounded by greenery. A small pond reflects the landscape, while a fire pit is visible nearby. Rustic wooden chairs provide seating, and smoke can be seen rising from the fire, creating a cozy atmosphere in nature.

Home in Goshen

Nature Lover's Paradise

4.95 out of 5 average rating, 201 reviews

A charming two-story house is adorned with twinkling lights, creating a warm glow against the snowy backdrop. A festive wreath is displayed in the window, while snowflakes gently fall, blanketing the front yard and surrounding trees.

Home in Rochester

The McKinley House

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 480 reviews

A cozy yurt is positioned in a snowy landscape, illuminated from within by warm light. The surrounding trees are silhouetted against the twilight sky, and the entrance to the yurt is visible, inviting guests to explore the warmth inside.

Yurt in Randolph

Upper Yurt Stay on VT Homestead

Superhost

A spacious room features two queen beds adorned with vibrant patterned comforters. A flat-screen TV is mounted on the wall. A window allows natural light to fill the space, while an air conditioning unit is positioned nearby. A wooden dresser and lamps add functional touches.

4.62 out of 5 average rating, 117 reviews

Killington Studio: Great Location! Comfy. 431

4.88 out of 5 average rating, 265 reviews

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

4.91 out of 5 average rating, 961 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.

Guest house in Granville

Moon Valley Country Retreat no clean fee pets yes

5 out of 5 average rating, 50 reviews

The exterior of the townhouse showcases a two-story structure with a sloped roof and large windows. A wooden deck features seating for two, inviting relaxation outdoors. Surrounding greenery complements the setting, while a stone path leads to the entrance.

Townhouse in Killington

Ski-in / Ski-out 3BDR+ Killington Condo at Sunrise

Superhost

An open living space features a bright red sofa with decorative pillows, complemented by a warm wood dining area with stools. The kitchen, equipped with stainless steel appliances, is visible in the background. Soft lighting creates a welcoming ambiance throughout the suite.

4.89 out of 5 average rating, 251 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

4.9 out of 5 average rating, 150 reviews

The exterior of a charming yellow house is surrounded by lush greenery and colorful landscaping. A stone pathway leads to the entrance, framed by well-maintained shrubs and ornamental features. Tall trees provide privacy and a natural backdrop, enhancing the serene outdoor atmosphere.

Home in Plainfield

Historic Home on 17 acres of land. Go escape!

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.

4.97 out of 5 average rating, 152 reviews

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

Private, pet-friendly home rentals

4.99 out of 5 average rating, 144 reviews

A small balcony features a blue bistro table with two matching chairs, accompanied by a vase of fresh flowers. Scenic views of rolling hills and lush greenery extend beyond the railing, while a wooden fence offers a sense of privacy.

Guest suite in Castleton

Vermont Hill Top Studio

4.96 out of 5 average rating, 207 reviews

The cabin is nestled among lush greenery and tall trees, featuring a wooden exterior with large windows. A sloped roof complements the natural surroundings, while blue skies and scattered clouds provide a serene backdrop for this private retreat.

Cabin in Woodstock

Hideaway Cabin by the Stream on 27 Acres

4.95 out of 5 average rating, 148 reviews

Cottage in Hartland

Adorable Dog Friendly Cottage w/FIOS

4.96 out of 5 average rating, 218 reviews

A cozy log cabin is framed by snow-covered trees, showcasing a steep, metal roof and rustic wooden exterior. The porch features wooden pillars and a welcoming entrance, creating a serene setting in the winter landscape.

Cabin in South Royalton

Cozy 4-season Cabin on Pond - "East Cabin"

4.95 out of 5 average rating, 123 reviews

The kitchen area features a central island with seating, surrounded by dark cabinetry and stainless-steel appliances. Exposed wooden beams and a sloped ceiling create an airy atmosphere. A dining area is visible in the background, adorned with a wooden table and comfortable chairs.

Loft in Randolph

Stylish factory-farmhouse deluxe loft

4.98 out of 5 average rating, 106 reviews

A cozy cottage is nestled amidst a serene winter landscape, surrounded by snow-covered trees. A gently sloped driveway leads up to the home, where a wrap-around porch can be seen. The scene captures the tranquility of winter in a rural setting.

Cottage in Rochester

Cozy cottage near Killington & Sugarbush

4.97 out of 5 average rating, 101 reviews

A log cabin is set amidst a snowy landscape, featuring a large wrap-around deck that offers outdoor seating. Snow blankets the ground and the roof, while evergreen trees frame the property, enhancing the secluded ambiance. The stone chimney rises from the cabin, suggesting warmth inside.

Cabin in Cavendish

Pine Ridge Log Cabin Minutes to Okemo & Killington