
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.

Private Getaway on Lake Lamoille
Tucked away on Lake Lamoille in Morristown, this beautiful brand new apartment is just minutes from town and yet offers tranquility and spectacular views. The lake is home to eagles, herons, geese, ospreys and fish! You will see kayakers out there fishing! Stowe Mt and Smuggler’s Notch are both nearby. Breweries, art galleries, restaurants are close by. You can walk or bike to the 93 mile Lamoille Valley Rail Trail from our home. Our shed is available for storing your bikes, kayaks or skis.

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 simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

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.

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.

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.

Jay Peak 3 miles - ski home via Big Jay!
Best backcountry skiing in New England - mountain getaway with stunning views! • Jay Peak Resort 3 miles away! • Ski home from Jay Peak via Big Jay! • Backcountry ski 6 mountains from your door! • Tour Long Trail, Catamount Trail, Big Jay & Little Jay from here! • Backcountry guiding available (15% discount for guests!) Note: There is also an apt in the main house that sleeps 8. • Vermont Mountain Experience: guests get a 15% discount for photography, backcountry & resort guiding!

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***

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

Crofter's Green @ Jay Peak: O'Shea Farmhouse
The O'Shea Farmhouse is one of five micro-cottages at Crofter's Green - our small, thoughtfully-designed lodging property in the heart of Vermont. This cozy woodland retreat is just minutes from Jay Peak Ski Resort and the warm, eclectic town of Montgomery Center. this bright 2-story cottage sits at the forest's edge and offers a peaceful home base for exploring the Northeast Kingdom. It's simple, comfortable, and surrounded by nature. Find us on social media! @croftersgreen

Jay Peak Retreat
The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, and 3.5 from Boston.

Le chalet des bois, Peace and calm in the woods
Monumental open concept, in the heart of nature. Access to trails directly behind the house. Wood stove, large modern bathroom, one bedroom + sofa bed. Another sofa bed in the living room. Ideal chalet for a couple with children or two couples. Wild birds, turkey, and deer lovers welcome! Wifi and EV charger included. Dogs Welcome! CITQ : #308038
Popular amenities for Montgomery vacation rentals
Other great vacation rentals in Montgomery

New CleanAir Home on Highland Cattle Farm w. View

Owl’s Nest Cottage

Shadow Lake house

CITQ #302383 Chalet by Lake Brome

Carroll Cabin

The village chalet

Cute Waterview Flat by Jay Peak / Dog friendly

Private Log Cabin Chalet Near Jay on 14 Acres
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $336 CAD | $333 CAD | $333 CAD | $283 CAD | $286 CAD | $306 CAD | $294 CAD | $309 CAD | $314 CAD | $318 CAD | $263 CAD | $359 CAD |
| 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 $300 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 cabin rentals in Montgomery have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Montgomery. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Montgomery have free parking?
Absolutely! We offer over 10 bed and breakfast 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 $82 CAD per night before taxes and fees

Verified guest reviews
Over 5,240 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
90 of Montgomery vacation rentals include wifi 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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- Jay Peak Resort
- Owl's Head
- Mont Sutton Ski Resort
- Ski Bromont
- Jay Peak
- Zoo de Granby
- Bolton Valley Resort
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Stowe Mountain Resort
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Shelburne Museum
- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Bleu Lavande
- Parc Jacques-Cartier
- Lake Champlain Chocolates
- Waterfront Park
- Kingdom Trails
- Mont-Orford National Park
- Fairbanks Museum & Planetarium
- Spa Bolton
- Marais de la Rivière aux Cerises




