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Pet-friendly vacation rentals in Montgomery

Find and book unique pet-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 30 vacation rentals in Montgomery

  • Nightly prices starting at

    Montgomery vacation rentals start at G$23,021 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,010 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Montgomery vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Montgomery rentals

  • 4.9 Average rating

    Montgomery stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Montgomery

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

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Top guest favorite
An aerial view showcases the home nestled among vibrant autumn foliage, with red, orange, and yellow leaves contrasting against the tranquil lake. A private dock extends into the water, complemented by a row of chairs facing the scenic landscape.
Home in Eden
4.95 out of 5 average rating, 216 reviews

LakeView Manor

YEAR-ROUND outdoor in-deck HOT TUB! You’ll be ON THE WATER! Perfect for any size group. Spectacular sunsets from the covered porch or private dock. Relax in the OUTDOOR HOT TUB. Enjoy a peaceful lake view and listen to the loons. SKIERS, we are a short drive to three major ski resorts; Stowe, Jay Peak, and Smugglers Notch. Amazing restaurants and pubs are nearby, and a great general store is down the road. Bring your snowmobiles and snow shoes! Trails are everywhere, right outside the doorstep.

Top guest favorite
Home in Montgomery
4.92 out of 5 average rating, 124 reviews

Rustic Converted Barn near Jay Peak w/Pizza Oven

Located right on Main St. Montgomery Center, you’ll love our Barn because of its quaint and rustic Vermont country atmosphere. Ye Olde Barn has been lovingly renovated and updated while preserving and emphasizing its old farm charm. The Barn offers you the best value in town because of its size and its multiple living spaces. We are Vermonters and love our environment. We have installed solar panels/batteries to reduce carbon footprint. We strongly encourage you to recycle while in our home.

Guest favorite
The wooden cabin, characterized by a pitched roof and large front deck, is nestled in a grassy area surrounded by trees. A stack of firewood is neatly arranged beneath the deck, while a dog is seen exploring the green lawn.
Home in Westfield
4.95 out of 5 average rating, 262 reviews

Jay Peak 3 miles - secluded with spectacular view!

Mountains, streams & seclusion! • Hike the Long Trail • Road, gravel & mountain biking • Jay Peak Resort is three miles away! • Waterpark • Golf • Backcountry guiding - hiking, kayaking, gravel & mountain biking (15% discount) • Photography and videography (15% discount) This is the mountain getaway you dream about! Our only neighbors are animals in the surrounding mountains & forests. Note: There is also an apt in the main house that sleeps 8. Welcome to Vermont Mountain Experience!

Top guest favorite
The living room features tall windows that provide ample natural light and overlook the surrounding wooded area. A stone fireplace is flanked by a television and cozy seating options, including a leather sofa and lounge chairs. A patterned rug adds texture to the wooden floor.
Chalet in Westfield
4.97 out of 5 average rating, 146 reviews

Cozy Chalet at Jay Peak

The house is set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5br, 2.5 Bath, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting with panoramic mountain views once leaves have fallen. Seasonal Pool, Disc Golf, Volleyball, Playground & Hiking Trails a short walk from the house. 3 mi to Jay Peak. Air Conditioning is in three bedrooms which are installed by the 2nd Sunday of June then removed the last Sunday of Sep.

Top guest favorite
A green two-story house is viewed from a snow-covered path leading to its entrance. Thick layers of snow blanket the yard, while tall trees stand in the background against a clear sky, indicating a serene winter setting.
Chalet in Montgomery
4.93 out of 5 average rating, 141 reviews

Montgomery Meadows Chalet near Jay Peak

Located on beautiful, historic Hazens Notch Road, Montgomery Center, Vermont. This “hidden gem” of a house sets back from the road in a private setting on 5 spectacular acres of cleared land, with views of Jay Peak Ski and Golf Resort. A perfect location for skiing, hiking, biking, golfing, etc. Only 15 minutes from the resort and all of the great amenities (water park, ice rink, movie theater, climbing wall, arcade). Only 3 miles from local amenities (grocery store, top rated restaurants).

Top guest favorite
A spacious cabin is set in a lush green landscape, surrounded by tall trees. Large windows dominate the front, allowing natural light to fill the interior. The sloped grassy yard leads to a relaxing outdoor space, perfect for enjoying the serene woodland views.
Cabin in Enosburg
5.0 out of 5 average rating, 209 reviews

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away. You’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. Wake up to coffee on the deck or take a stroll around the pond. And you won’t regret kicking back in the evenings - star gazing is simply magical! We are certain that you’ll have a hard time leaving!

Guest favorite
A serene landscape shows several Jersey cows grazing on lush green grass near a pond. The water reflects the blue sky and distant mountains, while the surrounding trees add depth to the tranquil rural setting.
Farm stay in Fairfield
4.98 out of 5 average rating, 333 reviews

Organic Farm Hideaway Home and Pond

The house is tucked into the back of our 300-acre working dairy farm and offers breathtaking views of Mt. Mansfield. We are located in between two of Vermont's best ski resorts, Jay Peak and Smuggler Notch. Come for a winter adventure full of downhill skiing, riding or x-country touring. Stay for the local breweries, distilleries and restaurants. Or just relax at the farm, cozy up by the wood stove and cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

Top guest favorite
A spacious living room showcases original woodwork and a baby grand piano. Comfortable sofas and armchairs are arranged around a central table, with art displayed on the walls. A television is mounted near a window, allowing natural light to fill the space.
Home in Montgomery
4.94 out of 5 average rating, 279 reviews

Great Old Farmhouse near Jay Peak

Updated farmhouse built in 1860 located 8mi. from Jay Peak, in the heart of the village of Montgomery Center. There’s a bar/ restaurant & supermarket across the street but only the Trout River & forest out back. Easy access to skiing, mountain biking, hiking, and a quick walk to a great swimming hole. One of a few places locally with access to fast internet (Gigabit). The house, now solar powered, sleeps 6-8 and is spacious, well insulated, and well furnished. 8 people + 2 infants max.

Top guest favorite
The exterior of the lodge is presented, featuring light-colored siding and a covered porch area. Snow blankets the ground, while a stone accent column enhances the property’s charm. The bright red door contrasts with the muted tones of the surrounding wall and windows.
Apartment in Montgomery
4.94 out of 5 average rating, 154 reviews

The Original Montgomery Lodge - Tried and True!

     We are The Montgomery Lodge and we've been doing it right since 2008. That's 15 years of clean, affordable ski (and summer) lodging. Compare us to other area vacation rentals and you'll see that we cannot be beat. Located on Main Street in beautiful Montgomery Center -- the heart of the Jay Peak Region and gateway to VT's North East Kingdom! Walk to shops, grocery, bars, restaurants, spas and enjoy a rare, genuine, non-commercial ski-town experience that will beg your return.

Top guest favorite
Two unique chalet structures, designed with a modern aesthetic, are situated on a sloped landscape. The buildings feature angular shapes and large glass windows, which reflect the surrounding forest, inviting nature indoors. The ground is covered with natural foliage and rocks.
Chalet in West Bolton, Quebec
4.99 out of 5 average rating, 255 reviews

La Binocle: Peaceful Architect Cottage

Cosy timeless chalet conceptualized by the architects of _naturehumaine. Nestled into the cliffside at an altitude of 490 meters (1600 feet), its unique design is distinguished by boldness and originality and fits with harmony in its environment. Surrounded by forest, the cottage offers breathtaking views of Mount Glen and the surrounding nature largely protected by the Appalachian Corridor. The perfect silent place to relax and unwind. Photo: Adrien Williams / S.A. CITQ #302449

Top guest favorite
Home in Richford
4.99 out of 5 average rating, 162 reviews

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Our guest farmhouse, located 1 mile from the Canadian border, is close to Jay Peak Ski Resort and Mount Sutton. Mountain and meadow views are spectacular! Here, you are perfectly poised to explore both the quaint, foodie-focused, Eastern Townships just across the border in Quebec AND the scenic back-roads, abundant lakes, family farms, mountain trails, local pubs, and old general stores of Northern Vermont. Or just enjoy the porch & peaceful atmosphere!

Superhost
The spacious living area features hardwood flooring, a large coffee table placed on a patterned rug, and a gas-burning fireplace. Windows adorned with light curtains allow natural light to fill the room. A dining table with four chairs is visible, enhancing the shared living space.
Condo in Jay
4.82 out of 5 average rating, 293 reviews

Cozy Jay Condo

Welcome to our Mountainside Jay condo! This cozy 525 sq foot studio has a queen murphy bed, a queen sofa bed & a gas burning fireplace. Located directly across the street from the golf course/nordic center, next to the Ice Haus & the Water Park. Walk to the tram in the morning. Great destination for a small family, couples getaway or just a place to rest your head after a long day skiing/boarding. Newly renovated bathroom. Sweet and simple. Pets welcome!

Popular amenities for Montgomery pet-friendly home rentals

When is the best time to visit Montgomery?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$64,458 GYDG$62,366 GYDG$56,506 GYDG$40,810 GYDG$47,088 GYDG$43,949 GYDG$44,158 GYDG$50,855 GYDG$46,670 GYDG$50,227 GYDG$50,437 GYDG$59,017 GYD
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