Holiday houses in Montgomery

4.95 out of 5 average rating, 129 reviews

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.

4.99 out of 5 average rating, 156 reviews

Cabin in Enosburg

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!

4.92 out of 5 average rating, 149 reviews

Home in Lowell

Orchard House retreat near Jay Peak

Relax and unwind in this newly renovated house with peaceful overlook on apple orchard, woodland and hills. There are over 10 acres to play (snowshoe, cross country ski, sledding, hiking or just relaxing) and only 20 mins. to awesome skiing or riding at Jay Peak! Two bedrooms across two floors. Relax in the deep claw-footed tub in the large full bathroom. Fully outfitted kitchen: coffee maker, refrigerator, microwave, gas stove with oven. Grill on deck. Washer & dryer. Wifi for remote working.

4.96 out of 5 average rating, 102 reviews

Cottage in Montgomery

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.

4.94 out of 5 average rating, 115 reviews

Chalet in Montgomery

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).

4.94 out of 5 average rating, 117 reviews

Cabin in Montgomery

Mountain Retreat On The Creek

The Jay Peak Retreat - Experience the Northeast Kingdom’s premier destination at Jay Resort, known for its record breaking snowfall and Vermont’s largest indoor waterpark. Upon arrival, welcomed by an open-concept layout perfect for intimate gatherings and après-ski relaxation. The cabin blends high-end resort luxury with tranquility and privacy. Inquire about our Speak Easy Cabin, 15 minutes away. Conveniently located 1 hour from Burlington, 2 hours from Montreal, and 3.5 hours from Boston.

4.95 out of 5 average rating, 145 reviews

Tiny home in Mansonville

La Cabine Potton

La cabine est un mini chalet de style scandinave qui plaira aux adeptes de la nature, du calme et des pentes de ski l'hiver comme le vélo et la randonnée l'été. Ce chalet a été conçu en harmonie avec son environnement. D'ailleurs, sa taille permet de profiter de la nature tout en réduisant son empreinte écologique. Avec ses deux chambres, son foyer, sa grande terrasse et son spa, il est tout équipé pour répondre à vos besoins. Venez relaxer dans ce logement unique! Certificat CITQ #311739

4.94 out of 5 average rating, 239 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.

4.9 out of 5 average rating, 161 reviews

Cottage in Westfield

Historic Schoolhouse Minutes From Jay Peak

After a long day of hiking, biking, or skiing, come take a swing at our charming historical cottage. Dating back to the mid 1800s it was one of the first schoolhouses in the area, today it is filled with all the modern luxuries one would need. Our quaint porch is perfect for bird watching or leaf peeping. The inside includes high ceilings, a bedroom and a cozy loft- both with queen beds. French culture is only a 10 min drive away; Vermont culture is abound with maple syrup and warm locals.

4.95 out of 5 average rating, 206 reviews

Tiny home in Hardwick

Alder Brook Cottage: A Tiny House in the Woods

From the moment you cross the cedar footbridge over Alder Brook, you'll know you're somewhere special. Featured in Boston Magazine and CabinPorn, Alder Brook Cottage is an inspired, rustic dream cabin located in the woods of Vermont's Northeast Kingdom. Surrounded by a crystal clear stream and 1400 acres of rugged forest, it is the perfect getaway for glampers looking to experience the tiny house life. Minutes away from Caspian Lake, Hill Farmstead Brewery & Craftsbury Outdoor Center.

5 out of 5 average rating, 262 reviews

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***

4.99 out of 5 average rating, 162 reviews

Chalet in West Bolton

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

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Other great holiday rentals in Montgomery

5 out of 5 average rating, 46 reviews

Cabin in Montgomery

Jay Stay- An 18 Acre Mountain Retreat by Jay Peak

JustinRating, 5 stars3 months ago

Really enjoyed Amanda’s place for our group ski trip to Jay! In the warm weather we were able to take advantage of the firepit with firewood on site. The heated garage with pingpong, boot warmers and small bar was awesome. A hot-tub would put this place over the top! We would stay here again for our next trip!

5 out of 5 average rating, 33 reviews

Home in Jay

Owl’s Nest Cottage

NicholasRating, 5 stars3 weeks ago

Absolute hidden gem of a stay at the edge of Vermont. Space was super cozy and we felt right at home instantly. If you’re looking for a quiet getaway and plan on making dinners instead of eating out this is the perfect space, the kitchen was really nice to work in, and was equipped with all the essentials and more. Brendan was a great host, I would absolutely recommend this space to anyone looking for a relaxing and cozy few days away from the city!

4.95 out of 5 average rating, 57 reviews

Cozy Cabin nestled in VT’s Green Mountains

BrettRating, 5 stars2 months ago

This was the coolest little cabin in the woods. Its looks are very deceiving from outside; I thought it looked like a pretty average cabin in the woods. Inside it was so nice and homey. It was extremely clean, had way more space than I thought it would, and was peaceful and quiet. Jay Peak was about 10 minutes away. Local restaurants were good. No AT&T cell service at the house but the StarLink internet was fast and worked flawlessly. Hot water was always hot, toilets always flushed. No issues at all

4.89 out of 5 average rating, 55 reviews

15 min to Jay Peak

BrendanRating, 5 stars3 months ago

Diane’s space was fantastic. Super close to Jay peak and a variety of shops and restaurants. Highly recommend!

5 out of 5 average rating, 14 reviews

Home in Troy

A Stay at Jay *No Cleaning Fee*

BruceRating, 5 stars5 days ago

I had a great stay here. The place was very clean and quiet—perfect for relaxing after a busy day. Everything was just as described, and I had no issues during my visit. Would definitely stay again!

4.95 out of 5 average rating, 22 reviews

Cabin in Montgomery

Carroll Cabin

MilesRating, 5 stars2 months ago

We enjoyed a great stay and look forward to future visits.

Superhost

Cabin in Eden

4.89 out of 5 average rating, 9 reviews

Simply Eden- cabin 1

TomRating, 5 stars2 months ago

Everything about our stay was outstanding and as advertised. We made last minute decision to do some Spring skiing at Jay Peak and stayed for three nights at Sherry's cabin. We literally booked the room at about 9pm the night before. Super easy to get into the cabin and Sherry's driving directions were spot on. The cabin was spotless and had all you need to be comfortable. It's about 30 minutes to Jay Peak and 15 minutes from the cool town of Montgomery. A great complimentary touch was a nice bottle of cabernet and a pint of Ben & Jerry's. We would definitely stay at the cain again.