
Holiday rentals with a kayak in Bennington County
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Top-rated Accommodation with a Kayak in Bennington County
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Holiday House Rentals with a Kayak

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton
We had a great vacation at Whitley’s Airbnb. The house was very clean, spacious, and provided lots to do. It was also great being so close to Mt. Snow. I highly recommend this house and would love to come back!

The Birdhouse Retreat w/Hot Tub
We had a great stay! The place was perfect, had plenty of space. Particularly loved the coffee bar which was well stocked. We took a day trip to Mass MOCA which was only about 30-40 minutes away.

Cozy Benedict Farm House by South Village Pond
Location was fantastic and exactly what we were looking for: a launching off point for a family weekend of outdoor (winter) activities. All while being great value and a short (<10m) drive into Manchester. Carl was a fantastic host and extremely communicative / welcoming. The digital guidebook with local suggestions was an incredibly handy addition. "Above and beyond!" Looking forward to staying at this property or one of the many other's that Carl hosts. Thanks!

Bear House at Stratton Mountain
We had an incredible weekend at the Bear House! Mari is a fantastic host- she was incredibly responsive, thoughtful, and went above and beyond to ensure we had a seamless and memorable stay. The house itself is perfect for a ski getaway- immaculately kept, spacious, and well-equipped with a generously stocked kitchen. It comfortably accommodated our group, making it ideal for larger families traveling together. Plus, the location couldn’t be better for skiers—just a short and easy drive to Stratton Mountain. We can’t recommend this place enough and would absolutely stay here again!

Dorset Hollow House
Amazing home in a beautiful location. Minutes to town, shops restaurants etc but feels like you're in the middle of nowhere. The house was equipped with everything we needed and beyond. Amy was an amazing host and made sure we had everything we needed. Will definitely be back.

The Mountain Escape
Great space! We were comfortable with a big group here, and loved being so close to the slopes. Hot tub seems new and is in great condition.

MT SNOW Chalet + HOT TUB + new upgrades for 2024!
We had a great weekend at Lisa's house! Lisa was easy to get in touch with and when she knew she might be out of touch she gave us an alternate person to contact. It's snowed overnight during our stay and we were plowed out early to get on the mountain for first tracks. The house is exactly as pictured on the listing, we were very comfortable, and the hot tub was key for relaxing after a day on the mountain. The house has a 80's feel to it, and the wood panelling gives mountain vibes. We had everything we needed for our stay and really enjoyed the time we spent together!

Rustic home near skiing & lakes, walk to downtown
Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!
Cottages with a kayak

Emerald Cottage @ Harriman Reservoir
We really enjoyed our stay at Michelle’s place. Overlooking a lake in a peaceful location, this was perfect for a small group looking for a reasonably priced Airbnb to stay while skiing at Mount Snow. The location was cool and I can definitely see this house being great for warmer seasons as well. One thing that stood out was the clarity of instructions provided by the host. Both the description of the property and what to expect, and the check in/out instructions are very accurate and helpful.

Fully renovated 1830's farm house
Bill’s place was perfect for our family as we celebrated our son’s graduation. It was clean and there were enough bedrooms and beds for everyone, a beautiful live edge table for all of us to gather for meals and plenty of common spaces.

Love the outdoors? This is the place for you!
We had a great stay at the property. Was exactly how it was described and in photos. Met all of our expectations. Owner was responsive and flexible. 30 min from MT snow and 15 from restaurants and shopping. Close to state park for walking. Beautiful and peaceful lake community. We would definitely stay here again.

Hiker Haven, Woodford modern home
I had an absolutely fantastic stay! The location was perfect—nestled in the heart of nature, it provided the ideal setting for a relaxing and peaceful getaway. The house was immaculate, with every room being perfectly clean and thoughtfully arranged. I loved how there was no clutter, which really added to the calm and inviting atmosphere. The property is an ideal retreat for anyone looking to unwind. The host was incredibly responsive and attentive, offering helpful tips and recommendations in advance that made our stay even better. It was clear they truly care about their guests' experience. Highly recommend this place for anyone looking for a serene escape!

Modern Cozy Cottage minutes from Stratton &Bromley
Karen and Robs little cottage was perfect for our month stay in Vermont. Secluded in the woods but also close enough to town and the ski mountains. We had a blast and Karen was incredibly attentive and responsive with any of our needs. 4WD definitely a necessity if you are coming in the winter/shoulder season months.
Cabin rentals with a kayak

Mount Snow Cabin with Hot Tub on Deck
It was a quiet, peaceful stay! Loved the hot tub!

Spacious Wilmington Cabin: Walk to Lake
My friends and I really enjoyed this location -- great fireplace and pit outside, really quaint spot. We also really appreciated the small touches that the host added (already had fire wood ready, some basic spices in the cabinets, and even though we didn't need them, they had tampons and toiletries available in the bathrooms). Would recommend and stay again.

Lakehouse Cabin on Lake Raponda
Stayed for a ski weekend at Mount Snow. Nice, clean comfortable place, and we enjoyed the wood stove after skiing. We would definitely recommend this location.

Private Wooded Cabin, 8 Mi to Sundance Ski & Town!
We stayed here for four days in August, and it was a great place for us. As someone who frequents this area for camping, I booked this weekend needing a cabin instead to accommodate other guests that do not camp. Plenty of room for everyone. This cabin was so tranquil and the sound of the water fall/river was perfect. It was quaint and cozy. The kitchen was stocked with plenty of cooking utensils, pots, pans, etc. bathroom and bedrooms are clean. The front porch and deck provided excellent outdoor space. The owner was so wonderful - texting us safe travels both check in and check out days and clear instructions on coming and leaving the home. I will gladly stay here again and am looking forward to doing so!

Lakefront House with Stunning Views and Great Room
We had a great stay at this Vermont cabin. It felt like home right away, and we quickly got comfortable in the cozy living area. We spent hours playing cards around the table, enjoying the fireplace. The showers were hot, and the kitchen was well-equipped, making cooking a breeze. We had a few questions which Eva responded to quickly. It was amazing that she was kind enough to offer a late checkout, too, so we could enjoy our last morning and breakfast together. All in all, it was a comfortable and relaxing stay.
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Lake George Expedition Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Canterbury Farm