
Vacation rentals in Montgomery
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Top-rated vacation rentals in Montgomery
Guests agree: these stays are highly rated for location, cleanliness, and more.

Hillwest Mountain View
We are close to Jay Peak and Canada including Montreal. If you like hiking, the Long Trail is close by. If you like star gazing you will love seeing the Milky Way in our backyard. Our house is good for both couples and families. We have a private hiking trail that leads down to a cool mountain stream where you can cool off. Take a dip in the nearby Hippie Hole or go fishing or canoeing in nearby lake Carmi. There are three bedrooms and a master bath with a spa tub. Wifi, fireplace and more.

Charming Cottage by Jay Peak
Quaint cedar shake cottage perfect for a couples getaway. Bright open floor plan, comfortable and tastefully furnished. Gas fired stove in living room provides warmth and ambiance while the queen size bed is incredibly comfortable. Great galley kitchen fully equipped with everything you need to prepare your favorite meal or if you're not in the mood to cook there's four restaurants within walking distance. Jay Peak is only 8 miles from door to door. Easy parking. Discount ski tickets available.

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.

Cady’s Falls Cabin
Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Secluded Luxury Treehouse - Hot Tub + Projector
Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

200 acre Stowe area Bunkhouse.
Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

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).

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.

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. When morning comes, enjoy your coffee while cozied up in front of the fireplace or stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

Trout River Lodge - Discount Jay Peak Lift Tix
Welcome to the Trout River Lodge! Check out the “Three Holes” swimming hole and waterfalls, just a few hundred yards up the river. We are located right in the heart of Montgomery Center, VT. Live music at the Snowshoe Pub, breakfast at Bernies, and groceries from Sylvester’s are all just steps away. You can also enjoy the mountain biking and hiking trails just minutes away! ***Discount vouchers for Jay Peak Ski. Price info can be found in the Photos section. It changes each year***

A true Vermont get-away cabin in the woods
Badger Cottage offers a true rustic Vermont experience nestled in the woods with spectacular views and a quiet and peaceful ambiance. Once a barn, carefully reconstructed on the owners’ property, and modernized to today’s standards, this post and beam cabin is warm and cosy in winter and cool in summer. Well behaved dogs are very welcome and will enjoy the walks in the woods. Covid vaccinations are required. The owners live in an adjacent house with their very friendly Border Terrier

The Binocular: 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
Popular amenities for Montgomery vacation rentals
Other great vacation rentals in Montgomery

Jay Stay- An 18 Acre Mountain Retreat by Jay Peak

Luxury Converted Country Church

Cozy Cabin in a Cabin • Near Jay Peak Ski Resort

Foote Brook Cabin - Off Grid & On The Rocks

Seven Sugar Maples

Cabinesque waterview flat /Jay Peak/Dog friendly

Foothills of Jay Peak apartment

Family-Friendly NEK Basecamp Near Jay Peak
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$59,580 GYD | G$59,580 GYD | G$56,444 GYD | G$43,483 GYD | G$43,901 GYD | G$47,037 GYD | G$45,155 GYD | G$47,455 GYD | G$48,291 GYD | G$48,918 GYD | G$40,347 GYD | G$55,189 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Montgomery?
Montgomery has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in bed and breakfast rentals in Montgomery?
Experience the best of Montgomery with our bed and breakfast rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Montgomery?
Four-legged friends are welcome in Montgomery. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Montgomery?
Yes! Work meets play with ease at over 30 vacation rentals in Montgomery featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do bed and breakfast rentals in Montgomery have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Montgomery. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Montgomery have a kitchen?
Absolutely! We offer over 10 cabin rentals with a kitchen in Montgomery. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Montgomery have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi in Montgomery. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Montgomery have free parking?
Absolutely! We offer over 20 house rentals with free parking in Montgomery. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Montgomery

Total vacation rentals
Explore 90 vacation rentals in Montgomery

Nightly prices starting at
Montgomery vacation rentals start at G$14,634 GYD per night before taxes and fees

Verified guest reviews
Over 5,810 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
90 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!
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- House rentals Montgomery
- Waterfront rentals Montgomery
- Jay Peak Resort
- Owl's Head
- Zoo de Granby
- Mont Sutton Ski Resort
- Stowe Mountain Resort
- Bolton Valley Resort
- Ski Bromont
- Jay Peak Resort Golf Course
- Parc Safari
- Jay Peak
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Pump House Indoor Waterpark
- Snow Farm Vineyard & Winery
- Spa Bolton
- Shelburne Museum
- Elmore State Park
- Shelburne Vineyard
- Mont-Orford National Park
- Cold Hollow Cider Mill
- Fairbanks Museum & Planetarium
- Bleu Lavande
- Waterfront Park
- Kingdom Trails





