Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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Guest favorite

Apartment in Jay, Vermont, US

4.86 out of 5 average rating, 295 reviews

Jay Apartment

Only 10 minutes to Jay Peak Ski Resort. Secluded in the woods right next to Starr Brook, yet only a 2 min drive to the Jay Village Inn restaurant and bar and the Jay Country Store. Fire pit with cooking grate next to the brook you are welcome to use weather permitting. Great hiking, biking trails, snow showing and Nordic skiing minutes away. Some trails are accessible directly from the property. Very comfy bed, wonderful place to sleep. . Vermont Meals and Rooms Tax ID number is MRT-10126712

Feb 13 – 20

€ 125 per night

Guest favorite

Home in Montgomery

4.96 out of 5 average rating, 116 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.

Sep 25 – Oct 2

€ 195 per night

Guest favorite

Cabin in Montgomery

4.93 out of 5 average rating, 42 reviews

Cozy Mountain Hideaway

“The Jay Peak Retreat” located up the road in the Northeast Kingdoms most hidden gem, Jay Resort with the highest annual snowfall in Vermont. Also the largest indoor waterpark. Upon entry you are greeted by an open concept modern layout best for intimate get togethers and Apres Ski! Our newly renovated cabin has all the comforts of a chic resort with the tranquility and privacy you've always dreamed of. In warmer month enjoy your private backyard oasis with modern patio furniture on the creek.

May 30 – Jun 6

€ 195 per night

Guest favorite

Home in Montgomery, Vermont, US

4.94 out of 5 average rating, 212 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 and supermarket across the street but only the Trout River & forest out back. Easy access to skiing, mountain biking, hiking, and just downstream from a great swimming hole. One of a few places locally with access to fast internet (Gigabit). The house, now solar powered, sleeps 6-8 comfortably and is spacious and well furnished. 8 people + 2 infants max.

Mar 20 – 27

€ 211 per night

Guest favorite

Chalet in Montgomery

4.94 out of 5 average rating, 100 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).

Jul 10 – 17

€ 201 per night

Guest favorite

Cottage in Westfield, Vermont, US

4.92 out of 5 average rating, 106 reviews

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.

Dec 6 – 13

€ 147 per night

Guest favorite

Cottage in Montgomery

4.96 out of 5 average rating, 95 reviews

Crofter's Green @ Jay Peak: Sugar Shack

The Sugar Shack is one of five micro-cottages at Crofter's Green nested on twenty-five beautiful acres of land just 7 minutes from Jay Peak Ski Resort and 5 minutes from the warm, eclectic town of Montgomery Center, Vermont. Whether you're looking for a relaxing escape from the hustle and bustle, or want a cozy home-base from which to ski, hike, shop, or explore the nearby cities of Montreal and Burlington, the Sugar Shack is your ideal destination. Find us on social media! @croftersgreen

Apr 26 – May 3

€ 119 per night

Guest favorite

Home in Montgomery, Vermont, US

5.0 out of 5 average rating, 228 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/Golf Round/Water Park. Price info can be found in the Photos section***

May 10 – 17

€ 331 per night

Guest favorite

Apartment in Montgomery, Vermont, US

4.93 out of 5 average rating, 120 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.

Jul 5 – 12

€ 145 per night

Guest favorite

Cabin in Montgomery

4.92 out of 5 average rating, 189 reviews

Remote yet convenient cabin

Escape to a remote yet convenient spot in the mountains. This cabin is an open space with a kitchen, bathroom, and loft bedroom. 1000 square feet of rustic coziness inside with all the conveniences. It is located on 15 acres with amazing views, walking/ hiking/ X country Skiing/ biking/ ATV/ snowmobiling options, foliage season, and a pond in the summer. While this cabin is situated outside of town, it is close to all the local restaurants and 20 minutes from Jay Peak Resort.

May 26 – Jun 2

€ 102 per night

Guest favorite

Apartment in Montgomery

4.83 out of 5 average rating, 93 reviews

Good Vibes: Ski, Ride & Save Lodging

Find serenity by the Trout River at our private swimming and fishing hole, located only 10 miles from Jay Peak! Downtown Montgomery has music, dancing and the First Trax ski shop. ATVs/snowmobiles are welcome. Walk to the Comstock and Fuller Covered bridges. Save money staying at Good Vibes; go out locally to the Black Lantern for dinner and drinks, or stay home to bbq and relax by our fire pit. Make your travels into an epic adventure here at Good Vibes Lodging!

May 6 – 13

€ 81 per night

Guest favorite

Chalet in Frelighsburg, Canada

4.91 out of 5 average rating, 296 reviews

Frelighsburg. Charming mountain log pavillon

SPECIAL RATE for APRIL & MAY: $99. This authentic 4 season log cottage with its large stone fireplace and 2 bedrooms can accommodate 4 people. Ideal for a couple with 2 children. Fully equipped. Large sunny terrace. BBQ. High Speed Wifi. An ideal place for nature lovers, for biking, hiking, skiing or just relaxing. A haven of peace and inspiration for writers, poets at heart and dreamers... Quebec Tourism Reference number : 297222

May 2 – 9

€ 95 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Montgomery vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Montgomery's top sights

The Belfry51 locals recommend

Bernie's Restaurant24 locals recommend

Snow Shoe Lodge & Pub26 locals recommend

The INN15 locals recommend

Big Jay Tavern28 locals recommend

Vermont Salt Cave Spa & Halotherapy Center29 locals recommend

Other great vacation rentals in Montgomery

Superhost

Home in Montgomery

4.9 out of 5 average rating, 31 reviews

Mountain Biking/Hiking Lodge by the Brook

Jun 11 – 18

€ 219 per night

Guest favorite

Home in Montgomery

5.0 out of 5 average rating, 13 reviews

The Cliff House, an après-ski cozy retreat.

May 2 – 9

€ 221 per night

Guest favorite

Apartment in Montgomery, Vermont, US

4.9 out of 5 average rating, 10 reviews

Cabinesque waterview flat /Jay Peak/Dog friendly

Dec 7 – 14

€ 199 per night

Guest favorite

Cabin in Montgomery, Vermont, US

4.99 out of 5 average rating, 89 reviews

Serene Mountain Cabin with Private Pond & Hot Tub

Aug 11 – 18

€ 813 per night

Guest favorite

Cabin in Montgomery, Vermont, US

4.95 out of 5 average rating, 44 reviews

Private Log Cabin Chalet Near Jay on 14 Acres

Sep 7 – 14

€ 328 per night

Guest favorite

Home in Montgomery, Vermont, US

4.9 out of 5 average rating, 94 reviews

Rustic Converted Barn near Jay Peak w/Pizza Oven

Oct 30 – Nov 6

€ 325 per night

Guest favorite

Home in Montgomery, Vermont, US

4.99 out of 5 average rating, 68 reviews

The Pagoda - A contemporary home in the woods

Aug 28 – Sep 4

€ 448 per night

Guest favorite

Condo in Westfield, Vermont, US

4.97 out of 5 average rating, 65 reviews

Northeast Kingdom Little Piece of Heaven

Aug 4 – 11

€ 116 per night

Show all

Quick stats about vacation rentals in Montgomery

Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
4.2K reviews
Nightly prices starting at
€ 47 before taxes and fees

Frequently Asked Questions

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 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.
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 apartment rentals in Montgomery?
Experience the best of Montgomery with our apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 house rentals in Montgomery have free parking?
Absolutely! We offer over 30 house rentals with free parking in Montgomery. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Montgomery?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with air conditioning, over 30 homes with free parking, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Montgomery?
Four-legged friends are welcome in Montgomery. Choose from more than 40 vacation rentals for guests traveling with pets.

Vacation rentals in Montgomery

Top-rated vacation rentals in Montgomery

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Montgomery vacation rentals

Stay near Montgomery's top sights

Other great vacation rentals in Montgomery

Home in Montgomery

Home in Montgomery

Apartment in Montgomery, Vermont, US

Cabin in Montgomery, Vermont, US

Cabin in Montgomery, Vermont, US

Home in Montgomery, Vermont, US

Home in Montgomery, Vermont, US

Condo in Westfield, Vermont, US

Quick stats about vacation rentals in Montgomery

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do cabin rentals in Montgomery have wifi?

Do cabin rentals in Montgomery have a kitchen?

Are there family-friendly vacation rentals in Montgomery?

How much does it cost to stay in apartment rentals in Montgomery?

Are there vacation rentals with a dedicated workspace in Montgomery?

Do house rentals in Montgomery have free parking?

What are the most popular amenities for House Rentals in Montgomery?

Are there pet-friendly vacation rentals in Montgomery?

Destinations to explore