Vacation rentals with a kayak in Windsor County

Find and book unique kayak rentals on Airbnb

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Popular amenities for Windsor County kayak rentals

House rentals with a kayak

Superhost
Home in Ludlow
4.87 out of 5 average rating, 46 reviews

Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo

LaurelRating, 5 stars1 month ago
David’s place was amazing! It was excellent for our group, and he was very communicative. Thanks so much!
Top guest favorite
Home in Cornish
4.95 out of 5 average rating, 19 reviews

Cornish-Windsor Bridge Retreat with Amazing Views

NicoleRating, 5 stars6 months ago
We had a lovely stay at Jonathan's place at a pretty much perfect time of year. The views were incredible! The home had a ton of character, and somehow managed to be cozy despite being huge. The view from the shower/bath did not get old! We would definitely recommend to friends and family looking for a getaway.
Top guest favorite
Home in Cavendish
4.98 out of 5 average rating, 48 reviews

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

RickyRating, 5 stars1 month ago
Awesome place! All the games in the basement gave us something to do while hanging inside the house. It’s great being able to come back after a long day of snowboarding and relaxing in the hot tub. The kitchen had everything we needed to cook. Only thing “negative” I could say is we couldn’t find any trash bags for the trash cans but obviously not that big of a deal. Overall I would 100% recommend and would definitely stay here again, without a doubt
Superhost
Home in Hartford
4.8 out of 5 average rating, 10 reviews

Pet-Friendly, Mountainside Home | Treetop Lodge

AnneRating, 5 stars5 months ago
We stayed here while visiting family in Hanover forThanksgiving. A spacious house nestled within an amazing wooded area. We had the pleasure of waking up to all the trees covered in fresh snow. All the more perfect because the house has huge windows lots of natural light. Highly recommend.
Guest favorite
Home in Plymouth
4.95 out of 5 average rating, 21 reviews

Ski Condo/Townhome in Plymouth/Killington, Vt

VanessaRating, 5 stars2 months ago
Super cozy home about 20 minutes away from Killington. Everything was as described in the listing, but the pictures do not do the living room justice. It’s a very large, spacious room with lots of natural light, very comfortable to watch movies and play board games in
Top guest favorite
Home in Ludlow
4.94 out of 5 average rating, 62 reviews

Valhalla

JasonRating, 5 stars1 month ago
Great house with plenty of amenities - perfect for a ski weekend with friends! Very clean and well stocked. Would rent again!
Top guest favorite
Home in Lempster
4.97 out of 5 average rating, 38 reviews

Cozy Crescent Cottage

PaigeRating, 5 stars3 days ago
Everything about our stay was amazing! The views were beautiful! The hosts were quick to respond whenever I reached out. They provided anything and everything you could think of! We had so much fun hiking on the trail to the small waterfall just minutes from the cottage, kayaking, and playing games they had. It was so nice to stay at a place that made us feel at home.
Guest favorite
Home in Woodstock
4.97 out of 5 average rating, 59 reviews

Dana Road House Sunlit VT Country Home w/HotTub

EstherRating, 5 stars4 months ago
Kat’s house on Dana road was the perfect place for our vacation to Vermont. Our family appreciated the clear instructions, helpful hints, and well thought out amenities. We really liked the Whisper Hill products in the bathrooms and made sure we went to the store in Quechee to buy some of the lotion before we left. We have stayed at a lot of AirBnB’s, but the house on Dana road was the most well equipped out of all of our stays!

Cottage rentals with a kayak

Cottage in Ludlow
5 out of 5 average rating, 12 reviews

Cheerful 4-br lakeside cottage- minutes to Okemo!

TimothyRating, 5 stars2 months ago
Beautiful, well equipped home on a lake. The house was very cozy with beautiful views of the lake and Okemo mountain. Bedrooms were perfectly configured for our family of 5, with plenty of bathrooms and seating areas throughout. House had great heating options (radiant heat, heat pumps and gas fireplace) to stay comfortable during a very, very cold week of skiing. We saw a bald eagle as well! Very easy to access Jackson Gore base area (5 minutes) and only a few more to the main base area. 10 minutes to town. Couple great restaurants nearby. Host was very responsive and accommodating. We arrived during a massive snow storm and Chris was very helpful addressing issues with plowing and shoveling of driveway/walkway. One thing to note is that the house is located on a gravel/dirt road. You need a 4WD vehicle with proper tires to access this area safely during bad weather. Would stay again!
Guest favorite
Cottage in Acworth
5 out of 5 average rating, 17 reviews

Classic lakeside cottage with gorgeous sunset view

KirstenRating, 5 stars9 months ago
We just got back from an amazing few days at Breezy Pines. Mary was always quick to respond to any questions I had. The cottage was well equipped from kitchen supplies to comfortable linens and towel, Wi-fi, as well as wood for the fire pit. We enjoyed lazy days lounging in the sun and swimming. Meals were enjoyed on the screen porch overlooking the lake. Amazing sunset views. We enjoyed every minute of our stay.
Cottage in Mount Holly
5 out of 5 average rating, 8 reviews

Cozy and Cheerful 3 bedroom bedroom getaway!

RyanRating, 5 stars2 months ago
We had a great family ski trip and stay here. Amy was very proactive and communicated ahead of our arrival. The home was nicer than the pictures and the sauna was great. We'd gladly stay again.
Cottage in Ludlow
4.99 out of 5 average rating, 71 reviews

Cozy 2-BR Vermont Lakefront Cottage, 50 Mbps Wifi

JacquelineRating, 5 stars3 months ago
We had a lovely stay and Ken's place was the perfect location for a weekend of skiing at Okemo! The size of the cottage was perfect for 4 and included all the amenities (bonus points for an extra well stocked kitchen) we could've asked for. We will be back!
Guest favorite
Cottage in Londonderry
4.88 out of 5 average rating, 68 reviews

Vermont Country Cottage(Near Village w/Magic View)

KristinRating, 5 stars2 days ago
Even better than described! We had such a nice stay in the cottage. It’s absolutely adorable and has everything you could need for a night, a week or a month. Very clean and perfectly situated for privacy but close to attractions. Will definitely book again

Cabin rentals with a kayak

Top guest favorite
Cabin in Weston
5 out of 5 average rating, 34 reviews

Beautiful Log Cabin in Weston, VT

LauraRating, 5 stars3 months ago
Don't hesitate to book this beautiful cabin! We spent several days in Weston at Andrea's place and it was perfect. The cabin was clean, cozy, and had all the modern amenities we wanted. The layout is wonderful and it was great to have a bedroom and bathroom on the first floor for my elderly parents. The location is very peaceful and really gives a feeling of privacy, even though it's just a few minutes away from downtown Weston and Londonderry. This was a truly outstanding Air BnB with every detail attended to. If we are in Weston again, we will definitely stay here!
Guest favorite
Cabin in Ludlow
4.99 out of 5 average rating, 67 reviews

The Treehouse, Cozy Cabin on Lake Rescue

KellyRating, 5 stars3 months ago
Perfect spot for a ski weekend!! Just minutes from Okemo, beautiful and peaceful location. Great communication from Jessica on all things house related as well as things to do nearby, restaurant recommendations. House was full of amenities, felt right at home. We will be back!
Guest favorite
Cabin in Cavendish
4.96 out of 5 average rating, 55 reviews

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

NaomiRating, 5 stars3 weeks ago
This is a wonderful, peaceful cabin! We so appreciate Wendi’s attention to detail. The whole design was tastefully done. The hot tub was perfect! You get the feeling of cabin in the woods but in a luxurious way. My husband and I had the perfect getaway weekend!
Guest favorite
Cabin in Ludlow
5 out of 5 average rating, 10 reviews

Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!

PaulaRating, 5 stars1 month ago
We had a wonderful time visiting Vermont. We were able to ski, explore the area and have some great time as a family. The cabin was exactly what we needed, and we will certainly be returning. Thank you for sharing this treasure with us. Instructions were very clear and we appreciate your proactive communications. Thanks for some great memories.
Superhost
Cabin in Barnard
4.8 out of 5 average rating, 15 reviews

Private post & beam log cabin on Macintosh Pond.

NinaRating, 5 stars3 months ago
It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!
Guest favorite
Cabin in Mount Holly
4.98 out of 5 average rating, 46 reviews

Lake House near Ludlow/Okemo and Killington

PaigeRating, 5 stars2 months ago
We had a lovely stay at Ambers place. Her home is extremely cozy and homey—the perfect vibe for a lake / ski weekend. It’s very spacious (the photos don’t do it justice), had a well stocked kitchen, and a pretty lake view. About 10 mins from Okemo and 30 mins from Killington. Would definitely recommend!
Superhost
Cabin in Stockbridge
4.86 out of 5 average rating, 22 reviews

T’s Hideaway

LucasRating, 5 stars2 months ago
Loved our stay!
Guest favorite
Cabin in Killington
4.93 out of 5 average rating, 57 reviews

Brand New Creekside Cabin at Killington

J.B.Rating, 5 stars1 month ago
We loved the "net cabin"! Plenty of room for everyone. So easy to get to Killington, Woodstock, & restaurants. We felt right at home. Highly recommend!

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