
House holiday rentals in Montgomery
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House rentals with a pool

Sutton Hideaway: Opulent Mountain Couples Retreat
Our stay was absolutely magical - from the clean, comfortable, stylishly well appointed home to the gorgeous surroundings, we loved every moment. David was also wonderful, gave clear instructions and was very responsive. 11/10 would recommend - we can't wait to visit again!

Maison Greenwood CITQ 172351
This is the second year we've stayed at Andree-Anne's for our annual golf tournament. The place is perfect for us and if we play in Estrie again in the next few years, we will go to Andree-Anne's!!

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak
This place was perfect for our family of three for a long weekend. The room had everything we needed and the views of the village from the balcony were amazing. Lots to do in the village and plenty more just a short drive down the road to Stowe. We’d love to come back in the summer when there are more outdoor activities available.

The Vista - 180º Mt. views w/Pool 12min to Stowe
Look no further if you're traveling with toddlers—this Airbnb is a dream for families! The location is perfect: tucked just outside of Stowe, it offers peaceful country vibes, a spacious backyard, and stunning mountain views from every window—all while being just a short drive from town. What really sets this home apart is how toddler-friendly it is. It's a BabyQuip heaven—stocked with everything from a high chair and nugget couch (iykyk!), to Fisher Price Little People toys, coloring supplies, a train set, games, and more. Our toddler had a blast and was perfectly content spending evenings at the house, thanks to the endless entertainment options. The host went above and beyond—the home was spotless, and the kitchen was fully equipped with all the essentials. Highly recommend for any family looking for a relaxing, kid-friendly escape in Vermont!

Charming Sugarbush Standalone Condo
Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

Beautiful home with spa, pool, fire pit, game room
Michael and Shayna are great and responsive hosts. The house is as beautiful, airy and large as per the pictures. It is absolutely impeccably clean! The kitchen is fantastic! The location is calm and private with nice landscaping, birds and even a mini pond with frogs. At night, we heard the loons. There are many varied spaces to discover and enjoy, inside and outside, such as the inviting large game room, the pretty solarium or the outside decks. We went kayaking in the interesting bay and had fun going under the covered bridge and to Whetstone island. We opted to use the nearby boat ramp at Forand park as an easier way to put the kayak in the water. There is a walkable small access to the bay which is a good place to bring paddle boards. It was still early in the season and the small deck wasn't installed yet. Finally, we enjoyed getting smoked fish at Keet Baird just a little down the street. Thank you for the great escape and welcoming us in you house!

EPIC Stowe Getaway - Great For Families & Friends
weekend family trip for 6 of us and our dog(4 adults and 2 kids), plenty of space for everyone, and much larger than I expected! we enjoyed cooking in the well stocked kitchen, playing board games on the large dining room table, swimming in the pool and soaking in the hot tub, wrapping the nights up with a movie on their Roku TV! Kristin was very responsive in her communication, we had a lovely time and would love to plan future trips here again!

The Blue Mountain Lodge, 6 bedroom, 4 bathrooms...
What an excellent spot. Our group had the best time and we’d love to return!
Weekly house rentals

The striped owl
Amazing home. We had a very relaxing time here. Alain was responsive and helpful. Would absolutely come back.

Owl’s Nest Cottage
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!

Cozy Cabin nestled in VT’s Green Mountains
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

The Red House- PEACEFUL WOODED JAY PEAK AREA HOME
What a beautiful place! We enjoyed Chris's place as a lovely retreat after long days of skiing. The kitchen was well-appointed, the wood stove was so enjoyable, and the kids loved all the games, pool table, and dart board. Here's hoping we can plan another trip there again next year!

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

Ohmland
A perfect private little getaway in a remote location. It was exactly what we were looking for to get away from the stress of life for a bit. A rustic farmhouse with lots of land for the dogs to roam. We felt right at home and the host was very kind.

The Jay’s Nest, beautiful and unique.
Great place to stay, we all had a wonderful time.

The Gambrel Mountain Retreat at Twin Ponds
Absolutely breathtaking. The views were stunning, the space amazing. As soon as I walked in, I planned my next trip.
Private house rentals

Pur Nature Owl's Head et Spa
Peaceful, beautiful and quiet, will definitely go again

Hot tub with stunning views!
This was a gorgeous home away from home! Spectacular views of Jay Peak nestled in the woods of a quiet neighborhood. We had a few minor questions/concerns while there that were quickly answered/resolved with the management team who were very responsive. The bed layout could’ve been explained a bit better - somewhat unclear prior to arrival based on drawings and explanations available online. We actually had more room to spread out than we realized in advance. If you enjoy cooking the cookware left some room for improvement but met our basic needs. Being able to park in the garage was an added bonus. Great experience - would definitely recommend and would go back!

Relaxing Craftsbury Retreat
We have stayed at Neal’s place multiple times in the spring and fall, and have always found it to be convenient and cozy. This time, unexpected snow and a town-wide power-outage made the propane fireplace, battery-powered lantern, and handheld flashlight more than just ambiance-enhancers! They were peace-of-mind enhancers! Thank heavens we had received our Chicken Confidential sandwiches at Black Bird Bistro (a MUST every time we’re in town!) five minutes before the outage. Vacation saved!

Cottage – Le Refuge (Off-Grid)
The cottage is very beautiful and well maintained, my boyfriend and I had a great weekend, there are several walking shelters within walking distance of the cottage. The cottage offers many things to do too! We really enjoyed it and want to come back again!

Cozy eco-friendly house in Sutton
Etienne and Kim's house was perfect for a quiet weekend with friends. The place is warm, relaxing and welcoming.

Vermont Mountain Retreat, Ski Cabin
We really enjoyed stay at Amra’s place! We would definitely go back again! Only a half an hour from Jay Peak. Amra’s communication the whole trip was impeccable. We really felt at home!

Cozy home with mountain views
Great little secluded place for a quiet, relaxing time, but also very close to Stowe and a number of great shops and restaurants. Joe was very responsive and actually brought me a water hose so I could fill my cold plunge. I enjoyed my stay and would recommend to others looking to unwind.

Mountain Tiny Home Lake Retreat
This was our 3rd stay on Metcalf Pond but our first at Loonshead. The camp is very clean and comfortable; its location right on the water, among the mountains, is incredible. The drives to the area small towns and sites are peaceful and gorgeous. It's truly a privilege to be able to spend time on the Pond. We very much look forward to returning.
Quick stats about house rentals in Montgomery
Total rentals
20 properties
Nightly prices starting at
₹12,088 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Jay Peak Resort
- Smugglers' Notch Resort
- Owl's Head
- Mont Sutton Ski Resort
- Ski Bromont
- Parc Safari
- Amazoo Park
- Bolton Valley Resort
- Jay Peak Resort Golf Course
- Spruce Peak
- Cochran's Ski Area
- Pump House Indoor Waterpark
- Sherbrooke Golf Club
- Le Vignoble du Ruisseau - Winery & Cidery
- Val Caudalies - Vignoble & Cidrerie
- Country Club of Vermont
- Vermont National Country Club
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Domaine Cotes d'Ardoise - Winery & Cidery
- Burlington Country Club
- Le Club De Golf Memphrémagog
- Pinegrove Country Club