
House vacation rentals in Rupert
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Top-rated house rentals in Rupert
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Popular amenities for Rupert house rentals
House rentals with a pool

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Sunlit 4BD Centrally Located All Things Saratoga
Suzanne's place is amazing. Everything you need is available and the home itself is just beautiful. We will definitely come again.

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

East Side Escape with Pool & Deck
Joshua is home was perfect for our stay. We were especially grateful to him as he stepped up when our initial Airbnb had a pipe freeze and so we had to do a quick switch to a new Airbnb. Joshua was responsive and extremely helpful. His home is beautiful and exactly as described. We felt like we were in the lap of luxury with quality linens and towels. The home is within five minutes to everything in downtown Saratoga, which was also wonderful. There was an unexpected ice storm while we were visiting, and Joshua came and not only sanded and shoveled, but worked hard to chip away ice to ensure our safety walking to and from the driveway. We would love to come back another time and would definitely recommend Josh's home to anybody considering staying in Saratoga.

Beautiful Poolside Home near Lake George Saratoga
I can't say enough about how lovely Melissa's home is. The home is so spacious, clean and beautifully decorated. We needed a local place to stay unexpectedly and were able to do a same day booking at Melissa's. We're so thankful we found her place because it met every need we had. Unfortunately it was pretty cold and ended up snowing so we didn't get to enjoy the patio and pool area but hope to be able to come back sometime to do just that. I'd highly recommend Melissa and her home whenever you're heading to Saratoga. It was a wonderful experience all around. Thank you Melissa!

Time to Relax, close to Saratoga.
The house was beautiful and Rhonda was great, she was very responsive and helpful. We felt right at home and enjoyed the place more than Lake George :) , the hot tub and pool were great and i would recommend anyone coming to this area to definitely book the place if they get the chance.

Adorable house with pool
Perfect for our Easter family gathering! We especially enjoyed spending time in their delightful backyard cooking on their gas grill and admiring their exquisite flowering trees!

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Weekly house rentals

Private Adirondack Chalet Game Room and Bar/Lounge
We had an amazing time here! Our family and friends spent the weekend for our son’s birthday and we felt right at home. The house is so cozy and comfortable. Will most definitely stay here again!

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!
This place was beautiful, and so much bigger than the pictures!! We loved how private it felt, and it was just a short walk to downtown! Would recommend to anyone coming to this area, and would gladly stay again ourselves!!

Spring/Summer Fun Treasures Waiting
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.

Summit View Ski and Golf Retreat w/hot tub & Sauna
We came up to celebrate a 40th birthday. Jason’s home was absolutely beautiful and exactly what we were looking for. We had a great time relaxing playing games and soaking in the hot tub. Pictures of Stratton Mountain do not do it justice, it’s so much closer in person and stunning. We loved the fireplace indoors and the outdoor fire pit. We had great weather so we were able to utilize the fire pit and then fireplace at night when it was chilly. Very cozy vibes! We would absolutely recommend this gem and would love to come back! Also, Pearl’s Place Southern Kitchen was delicious, get the bbq!

Sunset Bay: Amazing waterfront w/ dock on 5 acres!
We stayed at Beth’s place in April. The place did not disappoint!! Beth thought of everything!! Our 20 yr old granddaughter stayed in the apartment. Absolutely great space. The view was stunning!! The place was extremely clean throughout. All the rooms are set up to relax and enjoy!! The basement was a wonderland for the kiddos. Every toy, game, and wide open space to play. It was a delightful stay.

Wilmington A-Frame- Cozy and Convenient
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!

Martin Ski Barn - 4BR Ski House, 15 min to Mt Snow
The house was extremely cozy and felt like a true ski house. It was fully stocked from cookware to card games and plenty of space to feel comfortable away from home. Alana was extremely pleasant to talk to and responded quickly to any of my questions. For our long stay, they had cleaners come to the home for an intermittent cleaning. As well as having the driveway plowed and salted after snow storms. The 15 min commute to mount snow is convenient and easy to navigate. I highly recommend staying for the great hospitality and the lovely home. I can’t wait to stay again.

Brooklyn Zoo: Unique retreat in the Berkshires
Our stay at Emily's place was great; all of the amenities that we needed, a great deck to hang out on, and a fully stocked kitchen. Would 100% book again.
Private house rentals

Country hideaway
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

Spacious Brattleboro home on river, walk to town
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

Clean, Captivating VT Farmhouse near Stratton!
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

Cozy Private House on Killington Mtn - Hottub
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.

DoubleDen - AC, Hot Tub, Game Room, Fire Pit
Dan & Holly’s place was the perfect Killington getaway! Ample space for our big crowd, very clean and well kept, very responsive hosts, and the perfect location for everything you need to do in Killington! Their guidebook also came as a wonderful resource for all things in the area! Would definitely stay again

3br/2ba Family Friendly home- 1mi from the track!
Brooke's place is a good size...lots of room and so many nice touches (especially the abundant amenities provided for a small child). Very clean. Just as pictured. All good. The only thing I'd say as a bit of info to a prospective Airbnb-er, is that this location is not a walk to town spot, unless you consider 1.7 miles to the main shopping/dining area walkable. That said, it is still incredibly convenient...super quick drive to town or to race track or the lake...all while staying in a quiet, woodsy neighborhood setting.

Central Haus (Group getaway on a quiet street)
Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

2 Bedroom House part of duplex in the Village
The staff at The Heritage were outstanding. Ray was god sent, he went above and beyond everyday. Not many left like him.
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Gore Mountain
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Saratoga Race Course
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Fort Ticonderoga
- Ekwanok Country Club
- Lake George Expedition Park
- Hooper Golf Course
- Dorset Field Club
- Huck Finn’s Playland, Albany
- Clarksburg State Park
- Peebles Island State Park
- Hildene, The Lincoln Family Home
- Pineridge Cross Country Ski Area