Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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Guest favorite

Home in Montgomery, Vermont, US

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.

May 5 – 12

G$35,572 GYD per night

Guest favorite

Guest suite in Sutton, Canada

4.93 out of 5 average rating, 104 reviews

Guest Studio with Beautiful Mountain Views

Our 30 acre farm property is located on a quiet country road just 6 kms from Sutton Village, a haven for cyclists, hikers, skiers and wine enthusiasts. The village features 2 brewpubs, a good choice of restaurants, fun shops and beautiful Mt. Sutton to explore. Enjoy spectacular views and sun rises from your private balcony or patio, the walking paths in our forest behind, cycle along the surrounding backroads or just enjoy some quiet time in front of the wood burning stove or outdoor fire pit.

Jun 24 – Jul 1

G$13,551 GYD 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.

Aug 8 – 15

G$34,918 GYD per night

Guest favorite

Chalet in Montgomery, Vermont, US

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 15 – 22

G$39,375 GYD per night

Guest favorite

Guest suite in Waterville, Vermont, US

5.0 out of 5 average rating, 112 reviews

Rivers Rock - a charming cottage in the woods

Warm, charming cottage, impeccably furnished with spacious cook's kitchen, nestled in a serene wooded hollow. Enjoy the cozy warmth of the gas fireplace in winter, the cool respite of river wading in summer, or brisk nights around the firepit after a day enjoying gorgeous fall foliage or biking on the Lamoille Valley Rail Trail. While rural, you're central: Smugglers Notch Resort 18 minutes, Jay Peak 30 minutes, Stowe Mountain Resort 40 minutes, Jeffersonville's art galleries 10 minutes.

Dec 18 – 25

G$36,318 GYD per night

Guest favorite

Cottage in Westfield, Vermont, US

4.92 out of 5 average rating, 108 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.

Sep 12 – 19

G$31,416 GYD per night

Guest favorite

Farm stay in Fairfield

4.97 out of 5 average rating, 327 reviews

Meadow Cottage on Organic Farm with Mountain Views

The Meadow Cottage is perched on a picturesque knoll in the back of our 300 acre working dairy farm. 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, restaurants and antique stores. Or just relax at the farm, watch us milk the cows or cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

Sep 6 – 13

G$28,974 GYD per night

Guest favorite

Home in Montgomery

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***

Jul 5 – 12

G$70,330 GYD per night

Guest favorite

Apartment in Montgomery

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.

May 28 – Jun 4

G$28,987 GYD per night

Guest favorite

Cabin in Montgomery, Vermont, US

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 11 – 18

G$19,838 GYD per night

Guest favorite

Condo in Jay, Vermont, US

4.82 out of 5 average rating, 187 reviews

Cozy Jay Condo

Welcome to our Mountainside Jay condo! This cozy 625 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!

Jun 10 – 17

G$15,911 GYD per night

Guest favorite

Apartment in Montgomery, Vermont, US

4.91 out of 5 average rating, 129 reviews

Dog Friendly Apartment near Jay Peak

Enjoy the beauty of Montgomery, Vermont while staying in a very spacious 1-bedroom apartment that is attached to an 1880s farmhouse with a large backyard, garden and and orchard. The apartment is a 15-20 minute drive to Jay Peak Resort and a 3 minute drive to a grocery store and restaurants. It is walking distance from the Hutchins covered bridge and there is private access to the river. Excellent walking for your dog(s)!

Jun 14 – 21

G$23,473 GYD 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

Guest favorite

Apartment in Jay

4.86 out of 5 average rating, 296 reviews

Jay Apartment

Sep 13 – 20

G$22,601 GYD per night

Guest favorite

Guesthouse in Highgate

4.98 out of 5 average rating, 528 reviews

Beautiful lake-front cottage, Lake Champlain

Mar 28 – Apr 4

G$22,384 GYD per night

Guest favorite

Apartment in Montgomery, Vermont, US

4.81 out of 5 average rating, 95 reviews

Good Vibes: Ski, Ride & Save Lodging

Oct 27 – Nov 3

G$15,575 GYD per night

Guest favorite

Cottage in Montgomery, Vermont, US

4.96 out of 5 average rating, 95 reviews

Crofter's Green @ Jay Peak: Sugar Shack

May 14 – 21

G$22,751 GYD per night

Guest favorite

Cabin in Montgomery, Vermont, US

4.93 out of 5 average rating, 44 reviews

Cozy Mountain Hideaway

Jul 7 – 14

G$35,670 GYD per night

Superhost

Home in Montgomery, Vermont, US

4.9 out of 5 average rating, 31 reviews

Mountain Biking/Hiking Lodge by the Brook

Jul 1 – 8

G$38,059 GYD per night

Guest favorite

Home in Montgomery

4.95 out of 5 average rating, 42 reviews

Cozy Cabin nestled in VT’s Green Mountains

May 30 – Jun 6

G$38,575 GYD per night

Guest favorite

Apartment in Montgomery

4.9 out of 5 average rating, 10 reviews

Cabinesque waterview flat /Jay Peak/Dog friendly

Nov 26 – Dec 3

G$40,163 GYD 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
G$10,428 GYD 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 house rentals in Montgomery have a kitchen?
Absolutely! We offer over 30 house 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 apartment rentals in Montgomery have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Montgomery. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Montgomery?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, 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

Apartment in Jay

Guesthouse in Highgate

Apartment in Montgomery, Vermont, US

Cottage in Montgomery, Vermont, US

Cabin in Montgomery, Vermont, US

Home in Montgomery, Vermont, US

Home in Montgomery

Apartment in Montgomery

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 house 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 apartment rentals in Montgomery have free parking?

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

Are there pet-friendly vacation rentals in Montgomery?

Destinations to explore