Pet-friendly vacation rentals in Stockbridge

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Top-rated pet-friendly home rentals in Stockbridge

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

The house is nestled among trees, reflecting a modern design with an asymmetrical roof. Snow covers the ground, creating a serene winter landscape. A small porch with a railing is visible, alongside large windows that hint at the interior's open layout.

Home in Waitsfield

4.91 out of 5 average rating, 149 reviews

Sweet Blue Mint Ski House

Beautifully designed 1800 sq mountain ski home on 2 acres at the end of a peaceful dead end in Hiddenwood. Minutes to ski slopes! 4 bedroom, 2 full bath with open, sunny layout! Huge stone fireplace, air locked mudroom, new hardwood floors, & windows galore inviting in the exquisite mountain views. Cathedral ceilings, ceiling fan, & pickled barn wood throughout. Fully equipped open cook's kitchen. Well cared for pets welcome! Pls note, all weekend stays require both the Friday & Saturday nights.

Guest favorite

A cozy living area presents a blue sofa facing a stone fireplace, which features a warm glow from the flames. Two gold side tables are positioned in front of the sofa, and a television is visible on the opposite wall, accompanied by rustic wooden beams overhead.

Cabin in Wells

4.94 out of 5 average rating, 192 reviews

Gatsby's Getaway

Ready to disconnect and recharge? Welcome to Gatsby's Getaway! Watch the sun rise over the Green Mountains and Little Lake from the comfort of your deck. If the weather disagrees, enjoy your coffee in front of the cozy fireplace in your charming bungalow, complete with cathedral ceilings and sliding glass doors. Close to hiking & biking trails, and many outdoor activities. 10 minutes to nearby Granville, NY or Poultney, VT. While not technically a 'tiny' house, it is a cozy cabin of 550sqft.

Guest favorite

A wooden deck is featured in the foreground, leading to a small sitting area with a patterned chair beside a black side table. Lush greenery surrounds the space, providing a natural setting, while a gravel path and stacked firewood are visible in the background.

Tiny home in Clarendon

4.9 out of 5 average rating, 226 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favorite

A stone fire pit is situated in a large grassy yard, surrounded by green trees and distant mountains. Flames flicker invitingly from within the circular arrangement of stones, offering a cozy focal point for gatherings.

Home in Mount Holly

4.92 out of 5 average rating, 118 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Guest favorite

The living area features a cozy sofa adorned with decorative pillows, positioned around a central coffee table. Natural light enters through a large window beside the door, illuminating the wood-paneled walls and rustic floor. A simple area rug adds texture to the space.

Cottage in Hartland

4.93 out of 5 average rating, 116 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a shared 20-acre sanctuary. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bathroom (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. 10% off for guests using only one bedroom (cannot be combined with other discounts). See details in property description. Dog sitting & walks sometimes available - please inquire for rates & info ahead of time.

Guest favorite

A single-story ranch home is surrounded by a lush green lawn, featuring a welcoming front deck with white railings. Dark shutters frame the windows, and colorful flowers add a touch of vibrancy to the landscape. A patio area is visible in the background.

Home in Manchester

4.85 out of 5 average rating, 230 reviews

Keys to Vermont

We have the keys to a great vacation in Southern Vermont, located in a quiet family neighborhood within walking distance to Manchester designer outlets. “Mom’s Place” is a three bedroom two bath ranch, just minutes from several major ski resorts, beautiful hiking trails , parks and recreation areas. Two minutes from some great restaurants and bars. The house has a fully equipped kitchen, laundry , Wi-Fi and is dog friendly. Come enjoy all Vermont has to offer in the comfort of Mom's home.

Guest favorite

A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.

Home in Plymouth

4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views! Ideally located between Killington (7 miles) & Okemo resorts and near Woodstock. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps. Direct access to the Green Mtn. Forest. NEW There's a picnic table near the water falls and Buddha Rocks. Bring lunch and enjoy your own nature paradise! Small private beach!

Superhost

The farmhouse, featuring a green metal roof, is set amidst vibrant autumn foliage. A front porch with seating is visible, along with a well-maintained lawn leading to a spacious yard. The surrounding trees showcase a blend of colors, enhancing the natural beauty of the property.

Home in Warren

4.84 out of 5 average rating, 230 reviews

Vermont Escape, Too

Traditional Vermont farmhouse nestled in the Mad River Valley walking distance to Warren village and minutes from Sugarbush Lincoln peak. Walk along the 3.8 acres of private woods adjacent to the mad river for a swim or sit on the back deck enjoying your morning coffee listening to the birds. 10 Min walk to Warren store and a less than 5 Min drive to Warren falls, Sugarbush, or hiking trails. Ideal home for all size groups looking to experience Vermont in this charming 1800's farmhouse.

Guest favorite

A serene sunset is reflected on the lake's surface, creating rippling patterns of orange and yellow. The silhouette of mountains is visible in the background, enhancing the tranquil atmosphere captured in this lakeside scene.

Home in Bridport

4.87 out of 5 average rating, 111 reviews

LakeFront, Endless Views, 3 level, open floor plan

This year-round timberframe lake front home is located on a private dead end road with spectacular views of Lake Champlain, the Crown Point Bridge and the Adirondack Mountains. It easily sleeps 8+ so it’s perfect for families, big groups, and well behaved furry friends. There are three bedrooms with California kings plus one queen sleeper couch in the separate living room. There are picturesque views from all 3 levels to enjoy sunsets, sunrises and the resident Bald Eagle soaring by.

Top guest favorite

A cozy living and dining area is portrayed with wooden floors and large windows. A plush sofa, centered on a geometric area rug, faces a flat-screen TV mounted on the wall. A dining table with chairs is positioned nearby, complemented by a small side table and a heater.

Apartment in Royalton

4.98 out of 5 average rating, 182 reviews

Quiet Vermont Get Away

This space is ideal for a family or friends. This is a dog-friendly apartment located above our garage with stairs. Just 5 min off Exit 3 on I89. Full kitchen to make family meals. Cozy living/dining space. Come and stay for skiing, snowmobiling, hiking, biking, golf, local breweries and so much more depending on the season. Close to Vt Law School. 35-40 minutes to Killington, Pico, Stowe, Bolton and Sugarbush. 20 minutes to Quechee and Woodstock. Sleeps 5/6 with using a bunk bed.

Top guest favorite

A spacious blue-clapboard home with a sloped roof is surrounded by manicured green lawns. Large windows are visible along the lower level, allowing natural light to illuminate the interior. The outdoor landscaping features decorative stones and a small flowering bush.

Home in New Haven

5 out of 5 average rating, 117 reviews

Beautiful timber frame just minutes to Middlebury!

This large, gracious home was custom built in 1987 and was fully renovated in 2019. Gorgeous post and beam construction with endless windows and mountain views! Enjoy the large kitchen surrounded by a great room & solarium. 6 bedrooms with 3.5 baths can accommodate a crowd. Mudroom with custom lockers. Enormous fire ring with Adirondack chairs. Central heating/AC, super fast WiFi . 5 mins to Middlebury. Home is on 25 acres, providing privacy and peace. Making memories is easy here!

Guest favorite

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

4.91 out of 5 average rating, 162 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Comfortably accommodates 12 people. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains!