
Holiday rentals with a kayak in Windham County
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Windham County
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County kayak rentals
Holiday House Rentals with a Kayak

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.

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!

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!

Gorgeous Vermont Lakefront with epic sunsets!
We've just been gone a day and I already miss this place. It was a beautiful home in the Green Mountains on a lake with mountain and sunset views. Now we want to come in the fall for the fall colors. It has a large yard, has privacy and we felt very safe. All 3 bedrooms had full bathrooms and outdoor space/decks with views in each room. Lots of outdoor space in general. The house and property were so great that we really didn't want to leave to do anything. We did take advice of a prior guest who mentioned downloading the directions ahead of time. Our Verizon coverage had some limitations in the area, but the home wifi was solid. We enjoyed seeing deer, turkey and the geese/goslings. It was so fun to watch the family of 13 (11 goslings) and another with 3 goslings on a daily basis. The dock by the lake is a great spot to chill out, use the kayaks, etc... We enjoyed taking day trips to cute towns, exploring the area and just relaxing. Love this place!!! Highly recommend.

Hot Tub, Mtn View-Mins to Hiking, Biking &Swimming
We had a wonderful weekend. We hiked on Friday while we had beautiful weather, enjoyed grilling out & the hot tub. Saturday since the weather didn't cooperate we went for a drive & for lunch. Enjoyed the game room while having some local craft beers (we were fortunate enough to meet & taste beers from Twisted Horn, if they're open stop in). The house was spacious, we thoroughly enjoyed staying here.

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Bear House at Stratton Mountain

The Mountain Escape
Cottages with a kayak

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.

Blacksmith Cottage on Spofford Lake
We really enjoyed our stay at the cottage. The cottage was cozy and perfect for two, or a couple with kids. We did not know it did not have an oven but Ali provided us with the right tools to cook our dinner on the stovetop. The lake was steps away, but the weather did not accommodate swimming and kayaking. (Cannot control Mother Nature). It was an ideal location for our long weekend. The only downside was the highway noise. With the windows shut since it got chilly, it was fine. But morning one with windows open, it was noticeable. (But, we are accustomed to minimal noise at home). We are already thinking about a return next summer with a few family members being in neighboring cottages. And I did not mention the private beach which was fun to meet our neighbors and share happy hour with various kids playing in the sand and waves.

Tiny Cottage on Spofford Lake
Such a cute cottage! The cottage was clean and the beachfront was beautiful. Ali was very responsive and helpful. Great stay!

Woods Cottage-Private cheerful two bedroom cottage
Ron & Priscilla are fabulous hosts! Extremely friendly and kind. They really went above and beyond to make sure we were safe and having a good time. They saved us from a winter snow storm AND a black out! They even came by to clear the snow on the path from the car to the house. The amount of things they did to make sure we were comfortable was really above and beyond. We felt right at home. The house was cozy and comfortable. The area is private, quiet and the surrounding area is beautiful. I would highly recommend anyone to stay with them. If we had more time off, we wouldn’t hesitate to go back! They really made our stay special.

Cottage on Spofford Lake “Barn”
The cabins were terrific. We had three cabins as a group. They are across the street from Spofford Lake, which has a small beach and a dock. We had a terrific night hanging out on the beach while lighting a fire in the pit. We had a great visit at Copper Cannon Distillery (located down the road) and went on a few hikes.

Cottage on Spofford Lake “Library”
We had a lovely time at the Library cottage, sitting on the porch, walking the grounds. Nice to spend time right on the beach that has Adirondack chairs and a fire pit. Our host Ali was always available and helpful. The bunk bed layout was a surprise, but worked out fine. We’d love to come back, maybe even in the summer. Thank you Ali for a welcoming stay.

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.

Settlers Cottage on Spofford Lake
Ali was an amazing host and the cottage was awesome. Recently renovated, super clean and super cool. We would definitely stay here again. Thank you for a real good time!
Cabin rentals with a kayak

Farmhouse Cabin on Spofford Lake
Everybody loved the place, lean and peaceful. I would recommend visiting.

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.

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
This was the best airbnb I've ever stayed at (and I've stayed at a lot)! Everything was as described and the cabin is completely magical. My pup and I immediately felt at home. The cabin is adorable and comfortable and the setting is peaceful and rejuvenating. The cabin is very well-stocked and the host is friendly, helpful and responsive. There's plenty to explore on the property and beautiful town-maintained hiking trails at a park just a short distance up the road. The setting is quiet and a bit remote (just as I'd hoped) and the views are beautiful. The wi-fi worked well. I hated to leave and will dream about this cabin! Can't wait to come back!

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.
Destinations to explore
- Rentals with pools Windham County
- Rentals with outdoor seating Windham County
- Rentals with a hot tub Windham County
- Condo rentals Windham County
- Pet-friendly rentals Windham County
- Family-friendly rentals Windham County
- House rentals Windham County
- Farmstay rentals Windham County
- Rentals with an accessible height toilet Windham County
- Rentals with a fireplace Windham County
- Townhouse rentals Windham County
- Cabin rentals Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with a patio Windham County
- Bed and breakfasts Windham County
- Chalet rentals Windham County
- Beachfront rentals Windham County
- Rentals with lake access Windham County
- Rentals with beach access Windham County
- Apartment rentals Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Rentals with a fire pit Windham County
- Rentals with a washing machine and dryer Windham County
- Tiny house rentals Windham County
- Rentals with a sauna Windham County
- Rentals with an EV charger Windham County
- Private suite rentals Windham County
- Rentals with breakfast Windham County
- Fitness-friendly rentals Windham County
- Rentals with a kayak Vermont
- Rentals with a kayak United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Hooper Golf Course