Vacation rentals with a kayak in Windsor County

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Top-rated kayak rentals in Windsor County

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Guest favorite

Home in Killington

4.9 out of 5 average rating, 184 reviews

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Guest favorite

Townhouse in Fairlee

4.99 out of 5 average rating, 246 reviews

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

Set in a lovely 3 acre garden setting, our Airbnb is 1/4 mile from the lake and 23 minutes from Dartmouth College or the Ski-way. This private, comfortable apartment is built onto our house with its own entrance, hardwood floors, radiant heat, large windows, full kitchen and bath, & gorgeous garden views. The wrap around loft has 3 generous semi-private sleeping areas with 2 queens + 1 twin. A queen futon is downstairs. Rental includes pass to Treasure Island Recreation area & beach: 1.5 mi..

Guest favorite

Condo in Killington

4.98 out of 5 average rating, 100 reviews

SunBear- Ski on Ski off, Pool, Hot Tub, Game room!

A perfect perch on the mountain for families & friends to gather and enjoy the outdoors. Enjoy ski-on, ski-off during the snow season as part of the Sunrise Village next to Killington Resort's Bear Mountain base area. Quiet & relaxing during the summer - an ideal base for hiking, canoeing, apple picking, and taking in fall foliage. During the winter, ski down to the Sunrise Village lift, and ski off again straight to the condo. Enjoy streaming over the gigabit wifi while while the kids play.

Guest favorite

Home in Ludlow

5 out of 5 average rating, 25 reviews

AFrame w/ lake ~ 5min to Okemo ~ 15 to Killington

- New construction A frame centrally located for skiing, hiking, golf, mountain biking, or just relax by the lake (we share one acre lakeside with 4 other homes) - Great for families or couples with 4 bedrooms and 3 baths (plus a loft) stretched out over 3 floors - Fully stocked kitchen, wood burning stove, fire pits (we have 3) and nicely setback from the road for privacy - Loaded basement with pool, darts, ping pong, games and books, backgammon, etc. - Available canoe, SUP and life vests

Superhost

Cabin in Killington

4.91 out of 5 average rating, 44 reviews

Brand New Creekside Cabin at Killington

Architect designed new home in Killington, just 5 miles from the ski lodges. This unique place, surrounded by forest, sits right on a creek with beaver dams visible from the oversized porch. Quiet, peaceful, & private setting, with Mountain views & Applchn. trail just 200 yards away. Home designed to be social & fun - double height great room has a giant hammock/net suspended 10' above for lounging. Huge 2nd fl loft, & 3rd fl cozy kids loft. Walk out basement makes this a 4 story home.

Guest favorite

Cabin in Plymouth

4.91 out of 5 average rating, 11 reviews

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo

Rent a "room" at an inn or rent this private B & B cottage. Romantic Retreat~Rest & relax at this unique tranquil getaway. Exclusive~A Bed & Breakfast Cottage for 2 adults. 1 BR & 2 BA. Rustic charm, generous modern amenities. King bed, 2 bathrooms, fine linens, living/dining area, galley kitchen, fireplace, hot tub, outdoor shower, porch, fire pit, canoe, & dog friendly! Killington&Okemo15minutesWoodstock 30 minutes-Ludlow 10 minutes Overlooks Lake Amherst. Some features are seasonal.

Guest favorite

Home in Plymouth

5 out of 5 average rating, 7 reviews

Camp Amherst Ski and Lakeside Retreat

Our newly renovated lakeside retreat is the ideal place for an active yet relaxing getaway! The renovations paid particular attention to highlighting the beauty of the lake itself. Numerous windows/sliders on all three floors give breathtaking views of the lake. During warmer months you have a private dock for lake activities. For Winter visitors, Killington and Okemo resorts are nearly equidistant from the house. Don't forget that a firepit during any season is the perfect night cap!

Guest favorite

Home in Woodstock

4.96 out of 5 average rating, 56 reviews

Dana Road House Sunlit VT Country Home w/HotTub

Dana Road House: an idyllic 3BR/2BA VT country home Ideally located just 1.7 miles from Woodstock Village & 20 min. to Killington Skyeship. Gazebo with cedar hot tub, patio with dining , chiminea & BBQ Spacious open floor plan, chef's kitchen, 2 living areas, wood stove, Smart TV & WiFi. 3 comfortable bedrooms: a king master suite with jetted tub, queen room with brass bed and a double twin room. All amenities provided for your comfort & enjoyment. Follow on Social @DanaRoadHouse

Guest favorite

Guesthouse in Pomfret

5 out of 5 average rating, 22 reviews

Cozy, clean studio with picturesque Vermont views!

Lovely studio in the heart of the mountains! Our cozy and well-lit space is perfect for solo travelers or couples looking to explore all that Vermont has to offer. Enjoy a queen-sized bed, pull out sofa, kitchenette and a charming bathroom. 2 miles to the Woodstock Village and 1 mile to Saskadena Six (formerly Suicide 6). Experience local life with all the modern amenities you need for a memorable stay. ***In the winter months, 4 wheel drive or all wheel drive is mandatory.***

Guest favorite

Guesthouse in Norwich

4.9 out of 5 average rating, 30 reviews

Dartmouth Area River House

"Charming Two-Bedroom Apartment on the Ompompanoosuc River in Norwich, VT Inviting two-bedroom private apartment in an 1830s farmhouse. Just a short ten-minute drive from Dartmouth College, it provides a tranquil retreat. Key Features: Ideal for Dartmouth College alumni, parents, and community members due to its close proximity to the campus. Long-Term Rentals: Enjoy a discount for rentals exceeding two weeks, making it a perfect option for extended stays. Two Queen Beds .

Guest favorite

Home in Ludlow

5 out of 5 average rating, 22 reviews

Ludlow Lake & Ski Cottage - Adventure Awaits!

Relax and unwind at our charming cottage directly on Lake Rescue in Ludlow, VT. Enjoy stunning lake views, direct access to water activities (kayaks and paddle boat included!), with close proximity to Okemo Mountain Resort (5 min), Fox Run Golf Club (5 min) and Killington Mountain Resort (20 min). Perfect for your family or a group of friends to take advantage of everything the area has to offer. Our cozy house offers everything you need for your relaxing getaway.

Guest favorite

Cabin in Fairlee

4.94 out of 5 average rating, 126 reviews

Fairlee Log Cabin

Cozy Log cabin 0.2 miles from Lake Fairlee! This year-round cabin is a cozy getaway from the hustle and bustle of life. Just two hours north of Boston, and 30 minutes from Dartmouth, Lebanon, and the White River Junction. Additional amenities: -Clawfoot tub -Outdoor firepit -40 acres of land for hiking, mountain biking, snowshoeing, etc. -dog only friendly for a $40 additional fee -**as of 2/1/23 new oven and dishwasher :)