Vacation rentals in Montgomery

4.92 out of 5 average rating, 357 reviews

Cabin in Stowe

The Canopy House—Remodeled Vermont A-Frame Near Downtown

Awarded as one of the top Airbnb's in New England by Condé Nast and Boston Globe! Featured on multiple global publications. Watch the snowflakes fall from the comfort of the 6-person outdoor hot tub, with first-class stargazing to be had all year long. Back inside, the vaulted interior features OM Home Furniture, while a 50” TV with soundbar sits above a real fire. Less than a two mile drive to all downtown Stowe has to offer. 3 BD 2 BA modern A-Frame with two living rooms, 6 person hot tub, Fireplace, two new Roku TV's , soundbar, AC unit, WiFi, deck and back patio, rainfall shower, high-end mattresses, Sonos speaker and furnished by OM Home Furniture. Close to Main Street, 5 miles to Von Trapp, 9 miles to Stowe Mountain Resort and .5 miles from rte 100 to get you easily in and out of town. you will have access to entire house accept for one personal closet in back downstairs bedroom. Less than a 2-mile drive to downtown Stowe, this home is on a hill just off Route 100. Nearby Von Trapp is full of restaurants and other amenities. Ski and snowboard from Stowe Mountain Resort 9 miles away, with picturesque hiking in the summer. I would highly recommend a four wheel or all wheel drive vehicle. House is on a hill with a pretty steep road leading to it.

4.98 out of 5 average rating, 61 reviews

Townhouse in Stowe

Stowe Depot townhouse - Fireplace -Deck- Rec Path

Spacious Stowe Village townhouse, in walking distance to many shops, restaurants and Park. The Main suite has a King bed, 40" HDTV, and an en-suite bathroom with Jacuzzi tub. The second bedroom has a queen bed, 27" HDTV and an en-suite bathroom. Beautiful kitchen with granite counters, coffee maker and grinder. Living room features a gas fireplace, smart TV and nice furniture. There is a comfortable Murphy bed and an air mattress for additional guests, plus a nice covered deck to enjoy!

4.87 out of 5 average rating, 275 reviews

Guesthouse in Eden

Teeny Tiny Cottage on Lake Eden Water Front

This cozy cottage with loft on water front, $65 dollars per nights, Two night minimum is required. We have week or month reservations. Depending on availability there is rental of (2) paddle boats (2), kayaks, (1) two man canoe, dock spaces for rent for personal water craft. Travel to Burlington airport is one hour and Montreal airports is two hours. The cottage is centrally located between major ski areas, 30 minutes to Jay Peak Resort, Stowe Resort, and Smugglers Notch Resort.

4.93 out of 5 average rating, 139 reviews

Home in Eden

Cozy Lake Eden Retreat|Hot Tub|Wifi|Games|Pets OK

Enjoy a quintessential Vermont getaway at this lakefront home. It’s the perfect place for remote workers and families looking for a perfect base for outdoor activities. Relax in then hot tub & admire gorgeous lake views, and enjoy direct access to the water. Rainy days are no less fun, with a game room and fireplace to keep you busy. Lake Eden –Frontyard! Eden Ethical Dog Sledding – 8 Min Drive Stowe – 30 Min Drive Create Lasting Memories In Eden With Us & Learn More Below!

4.97 out of 5 average rating, 64 reviews

Condo in Cambridge

The Best View at Smugglers' Notch

Escape to paradise at my stunning condo nestled in the heart of Smugglers' Notch Resort! With easy access to skiing, snowboarding, disc golf, and breathtaking seasonal foliage views from the 270-degree second-story roof deck, your perfect vacation spot is waiting. Enjoy ultra-high-speed Starlink Wi-Fi, Cable TV, air conditioning, washer, dryer, dishwasher, Keurig coffee machine, and a fully stocked kitchen. With my dog-friendly policy, your furry friend can join the fun.

5 out of 5 average rating, 7 reviews

Apartment in Jay

Absolute best ski on/off at Jay.

Location, location, location. This 2br Slopeside condo is position A on the snowiest mountain in the east. Inside, you'll find 2 bedrooms featuring a queen bed and a twin over full bunk. The kitchen comes fully equipped to make meal prep a breeze. The cozy living room has a gas fireplace to warm up or relax and enjoy an après drink. Our condos always feature complete linens, towels, and essential sundries because no one wants to lug that stuff to their vacation.

5 out of 5 average rating, 55 reviews

Home in Cambridge

Sunning Home near Smuggs/Stowe & Wedding Venues

Welcome to the Mirador- our Vermont getaway! Escape to the picturesque beauty of Vermont and indulge in a memorable stay at our charming retreat. Located just a stone's throw away from Smugglers Notch and conveniently close to popular wedding venues, this inviting house provides a comfortable and convenient base for your adventures. With its charm, modern amenities, and breathtaking surroundings, it's the ideal place to relax and explore all that Vermont has to offer.

4.9 out of 5 average rating, 41 reviews

Home in Malletts Bay

Chic Modern Lake Getaway!

Luxurious sanctuary on the shores of Lake Champlain with panoramic sunsets, unparalleled Lake views and a sandy beach right out the back door. Offering 4 bedrooms and 2.5 bathrooms- hi-end getaway sleeps up to 8 people. Located on a quiet dead end street our private beachfront home offers everything you desire to relax, recharge, and get away from it all! Enjoy an open and bright first floor with full gourmet kitchen and breathtaking views from the wall of windows.

5 out of 5 average rating, 33 reviews

Home in Jay

Location! Newly Renovated Ski-in/Out by Waterpark

Completely remodeled in 2024. Ski-in / Ski-out. Cannot beat the location! Steps to the water park, ice rink, tram, restaurants, and bars. Enjoy an upscale two story, 3 bed, 2 bath family-friendly luxury condo with a private back deck & small yard. You do not have to use your car at all. Quiet corner unit with no one above or below you. Each guest will be given a unique door code prior to check-in. Kitchen & linens are very well stocked. Well behaved dogs welcomed.

Apartment in Waterbury Center

4.98 out of 5 average rating, 63 reviews

Sir Richards Waterbury Stowe 2 B Lake View Escape

A fun, filled, peaceful property surrounded by nature. Drift into an amazing, relaxed state sitting on the front deck listening to the water fountains & closeness to nature. Only the mountains, ponds, woods & lake on your side and in front of you. And yet, only 2 blocks from busy Route 100 attractions. Spacious 1200 sq. ft. 4 prs. snowshoes winter, 2 kayaks, & a canoe on the 6 1/2 mile Reservoir. Hiking & fishing summer & winter. "Memories Are Made Here."

4.97 out of 5 average rating, 645 reviews

Guesthouse in Highgate

Beautiful lake-front cottage, Lake Champlain

Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!

4.89 out of 5 average rating, 167 reviews

Townhouse in Stowe

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

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What guests are saying

Topnotch Resort Home with Garage, Grill and Patio

4.82 out of 5 average rating, 17 reviews14 months ago

We absolutely loved everything about our stay - the home and hosts were both impeccable. The home is jusy like the pictures- the quintessential ski condo. It is incredibly comfortable- the big beds were both luxuriously comfortable and all the other appointments were as well. The kitchen is incredibly well appointed for meals. We mostly did quick/easy meals. But, it would have been a joy to cook in the kitchen. Most importantly for us, the condo is GREAT for kids and families. It has everything you need for a comfortable stay with kids, including a high chair, crib and pack n play. The Topnotch resort and amenities are also aptly named - they are truly top notch! Last but certainly not least, Stowe resort homes was a fabulous host. They were incredibly proactive and responsive to any questions we had. It truly felt like they wanted us to enjoy our stay as much as we did. We enthusiastically recommend this home and host!

Townhouse in Stowe

What guests are saying

Contemporary Chalet - Open floor plan - Location!

4.9 out of 5 average rating, 41 reviews3 weeks ago

Great modern cabin in the woods. Being close to Stowe Mtn and the cute town (10 min) and reasonable distance to Jay Peak (75 min) made Jason's place an ideal location for skiing but also a peaceful respite from city life. It snowed every day we were there--at the end of March--total bonus for skiing and snow lovers. The layout of the house is perfect for spending time with others while cooking, yet more remote bedrooms for quiet. Lots of really thoughtful amenities like ski storage, drying racks, ample firewood, well-stocked pantry basics, extra towels, pizza oven, and more.

Home in Stowe

What guests are saying

Sunset Treehouse

5 out of 5 average rating, 20 reviews1 month ago

If you’re looking to ski at Bolton Valley, really tough to beat this location unless you’re right in the resort. Worked out very conveniently for our family of 4 (2 adults and 2 young kids). Cleanliness is important to us and the bathroom, kitchen, foyer, etc. we’re all in great shape and updated. King size bed was comfortable. Some of the bedroom furniture was a bit dated, but was livable given the rest of the nice amenities and overall cleanliness of the apt….and the location to the lifts… Lucas was very upfront about the fact that we would need to bring an air mattress of some sort for the kids. This worked out more than fine as we sat up the mattress in the living room. All in all, this apt would work out well for anyone wanting close proximity to the ski lifts…

Home in Richmond

What guests are saying

Quiet Smuggs Retreat Ski in/out

4.93 out of 5 average rating, 57 reviews1 month ago

The location was great, easy access to the Morse lift and village shops. Everything we needed was provided, even coffee! I was well prepared having rented places before but I didn't need most of my supplies because they were already on-site. The place was spotless and had plenty of bath towels and pool towels. Having a door code made it super easy to come and go. Highly recommend!!

Apartment in Cambridge

What guests are saying

Downtown Apt #2 near Smuggs Stowe Jay Peak

4.85 out of 5 average rating, 46 reviews2 months ago

Great spot, would rent again. Very cold winter nights in February, so really appreciated the two extra thick blankets provided. Outdoor stairs to the apartment are steep but were mentioned and explained in the advertisement. Clean, cozy, comfortable. Thanks, Chris.

Apartment in Johnson

What guests are saying

Burnt Mountain: modern getaway near Jay Peak

4.91 out of 5 average rating, 11 reviews1 month ago

I have stayed in a many rental properties over the years and I have never had a kitchen so loaded with everything a cook could ask for - very helpful! Amazing views and a 20 minute drive to Jay - just a great experience. The property is on a dirt road, which is no joke. Make sure you have the right vehicle for Vermont mud season and you will have the time of your life. Highly recommended!

Home in Montgomery

What guests are saying

Gorgeous! Spacious! TEN Rooms! 5BR/3BA Flat Rate!

4.85 out of 5 average rating, 34 reviews9 months ago

The house is lovely! Everything was clean, water pressure was great, the beds were very comfortable . There was plenty of space, so we could all find time for quiet and privacy, while also having plenty of gathering areas for the family to be together. The host was always available and responsive for any questions we had.

Home in Newport

What guests are saying

The Westside ~ Hot Tub | Beach | Private Dock

4.88 out of 5 average rating, 51 reviews7 months ago

We had a great 4-night stay at Kylie's townhouse! Plenty of room for 6 adults and 2 kids (and we hosted other family members for dinner each night). The listing was exactly as described. Beds were very comfy, kitchen was well equipped, plenty of parking, and Kylie was very responsive and helpful. The views of Mallett's Bay are stunning. It's easy to get to Burlington and surrounding amenities (grocery stores/restaurants/coffee/playgrounds etc). We would not hesitate to stay again.

Townhouse in Colchester

What guests are saying

Lovely 1 bedroom

4.97 out of 5 average rating, 67 reviews6 months ago

Highly recommended space and host! Kurt is hands down an A+ super host! We arrived in Burlington in the evening with having another Airbnb reservation that we found not to be a good fit for us! Frantically searching for other Airbnb accommodations for the night, several hosts had availability but showed no urgency to help us. Kurt literally stopped what he was doing to go and turn lights and heat on for us. He also left water, a couple beers, and creamer in the fridge for our morning coffee, which too was provided. The space is exactly how it was pictured. Clean, uncluttered, and beautiful! Kurt’s place has great location in a charming quiet neighborhood with driveway parking. Comfortable bed and great water pressure in the shower was also great to have! Finding this place last minute was the cherry on top of our amazing Burlington experience….and we will be back! Thanks again

Apartment in Burlington

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Stay near Montgomery's top sights

The Belfry51 locals recommend

Vermont Salt Cave Spa & Halotherapy Center29 locals recommend

Big Jay Tavern28 locals recommend

Snow Shoe Lodge & Pub26 locals recommend

Bernie's Restaurant24 locals recommend

The Black Lantern Inn23 locals recommend

Other great vacation rentals in Montgomery

4.98 out of 5 average rating, 56 reviews

Cottage in Derby

On Golden Lake Salem

4.95 out of 5 average rating, 84 reviews

Home in Milton

Waterfront * Sunsets * Private * Swimming/Fishing

4.82 out of 5 average rating, 45 reviews

Villa in Stowe

Beautiful 5 Bedroom Villa with Amazing Views

4.92 out of 5 average rating, 60 reviews

Home in Westmore

New Vacation Home w/Awesome View!

Villa in Venise-en-Québec

4.85 out of 5 average rating, 65 reviews

Spacious Lakefront Champlain lake with SPA

4.86 out of 5 average rating, 21 reviews

Home in Glover

Cheerful 5-bedroom house offered by Lakeside Haven

4.88 out of 5 average rating, 8 reviews

Cabin in Eden

Simply Eden- cabin 1