House vacation rentals in Rupert

Ending up booking this home to accommodate my family as we were traveling for a wedding- overall, it was such a positive experience. Even though it was October, the pool was heated! My kids loved it. We were able to enjoy the yard and amenities, and fit/stay comfortably in the house. The third bedroom is the basement, which has a separated indoor access- which ended up working out for our family situation in that my sister and brother in law were able to have their own separate space. Diana was so kind to even let us check in earlier than anticipated, as we were traveling from Philly and ultimately unsure of our exact ETA. She was very responsive and kind. The area was so beautiful and close to everything. (And only a 3 minute drive to the venue!) If we were to make our way up this area again, we would absolutely stay here. Thank you so much!

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!

We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Really just a great weekend! The house was spacious and perfectly accommodated our family. Also perfect distance from town where there is tons to do. Julie was available for questions and was so easy to communicate with. We were in the area to celebrate our son’s college graduation and really could not have selected a more perfect spot!

Great environment, quiet area, close to attractions and private. Clean and spacey house with enough things to do. Mostly every necessity is provided and more. Clear instructions posted around the house with friendly owners. I would definitely recommend from couples to families this house is perfect and has everything u need for a good getaway. Furniture is extremely comfy and the house is well insulated.

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.

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.

Beautiful home. Pictures don’t do this location justice. Booked for our daughters wedding being held close by for relatives traveling and ourselves to be close to wedding. Would highly recommend for anyone looking in that area. They have thought of everything you could possibly need. We were out at events more than at the home and I honestly with we had done another day to enjoy some down time in the beautiful home. Owners and local property manager were wonderful at communicating and making sure everything was cared for (we had no concerns, but having contacts if there were any)

The house was exactly what we were looking for. It was at most 8 minutes from the bottom of the mountain. Super easy to get to and fron everything at Killington. Classically, the first morning we forgot gloves, then skis, then a helmet. Doing the roundtrip from the mountain was easy. The house was exactly as discribed and perfectly appointed for a ski house. Kids loved the foosball table. Kitchen was easy to use and had plenty of fridge space, cooking areas, and seating. The two living rooms allowed people space to decompress differently. Bedrooms were well sized and had plenty of sleeping areas. The hot tube was hot! Simple Vacation was highly responsive and a great host. We couldn't have asked for more. It was exactly what we were looking for and we will be back.

We enjoyed our stay immensely! We visit Rutland often and will continue to stay here as long as it is available! Everything was better than anticipated!

Our stay was amazing. The scenery was beautiful, the cabin itself was well stocked and clean and our host was extremely responsive and helpful. We will definitely be returning in the future!

Brandon‘s place was very comfortable and in the downtown area on a nice piece of property. The inside was set up great!

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.

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!

Cleanly kept home. Hot tub works great (though panel can be hard to read). Little bit of road noise, not bad at all. Walkable to downtown if you cross over to Maple Ave. Basement layout is a bit quirky.

What a charming and quirky base for some time away.  It has a well-appointed kitchen, including a variety of ways to make your morning joe.  The entire home was spotless. We were even left with a fresh new sponge for the kitchen sink. We usually bring our own just in case. It’s such a small thing, but it makes such a big difference.  When we noticed we weren’t getting hot water, the property manager was there in under four minutes to fix it.  The house decor is a mix of mid century and modern minimalist, with fun touches everywhere you look.  Although we didn’t have the best weather, we enjoyed time at MASS MOCA, the Antique Emporium, Cheeky, The Bear & Bee, and The Plant Connector.  The people we encountered were all so nice and friendly.  We were looking forward to enjoying an evening under the stars at the fire-pit, but weren’t able to due to rain, but what a great backyard! Luckily, we had a variety of porches to hang out on, one of the benefits of an older home.

Absolutely perfect for a getaway for 2. Jason's place is comfortable, intimate, and convenient. Jason's attention to detail is great. Highly recommended!

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!

Everything as described. Easy to find. Easy parking. Private and well equipped. Host quick to respond.

It was perfect for my overflow guests attending a weekend family reunion!

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.

Our stay at Mian and Anthony ’s place was fantastic! The house was impeccably clean and well-stocked with everything we needed. Mian and Anthony were very accommodating and provided great local tips. If we ever find ourselves back in the area we will definitely stay here again.

We had a a great stay! House and location was extremely peaceful. We loved the hot tub, wrap around porch and massage chair. Wish we could have stayed longer. We will definitely be back!

First time renting a place this surrounded by nature, very peaceful and relaxing. Beautiful in the mornings, the sun really shines through. The creek behind the house is serene and a great spot to relax. Vasili was very fast and helpful with responses. Would definitely book again. 10/10!