Vacation rentals with a kayak in Rutland County

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Top-rated kayak rentals in Rutland 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!

Superhost

Bungalow in Castleton

4.79 out of 5 average rating, 321 reviews

Lake Bomoseen Bungalow

My place is nestled on a private road on Lake Bomoseen in beautiful VT. 50 minutes from Killington, Pico, and Okemo Mtns and close to Castleton University. You’ll love the cozy, one room guest cottage that awaits you. Although my house sits between the cottage and the lake front, the bungalow still offers beautiful lake views with a lake front patio area 50 ft down the driveway. Use my kayaks or bring your own, dock space available for small boats. Boat rental available at a local marina.

Guest favorite

Cabin in Middletown Springs

4.95 out of 5 average rating, 22 reviews

Mountain Cabin on River with 24 Acres

Enjoy this cabin in the woods on 24 acres overlooking the Poultney River. You will enter through the truly unique slate staircase into an open concept living area. Kitchen has all appliances and entertaining pieces. Bar overlooks the dining and living room with internet tv. Two bedrooms with king bed, twin bunk beds and full convertible sofa. Large deck surrounded by slate patio. Take a short walk to the waterfall or laze by the river. Enjoy the onsite trails for hiking, biking or off roading.

Guest favorite

Cabin in Castleton

4.96 out of 5 average rating, 67 reviews

Cozy stone faced cottage on Lake Bomoseen.

Perfect get away for two people. One or two children in addition is ok. Queen sized sleigh bed in bedroom. There is a twin sized daybed in a lower living room and a couch in the upstairs living room, not a pullout. Extremely cozy Boat slip, kayaks, a canoe, swimming and a fishing area are available 4 houses north of the cottage-100 yards. Pico/Killington, fishing, horseback riding, snowmobiling all close by. Truly a 4 season area to enjoy. Castleton University is 7 minutes away. NO PETS

Guest favorite

Condo in Killington

4.98 out of 5 average rating, 104 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 Poultney

4.93 out of 5 average rating, 121 reviews

VT Lake House living with sunset views!

Welcome to the Vermont Lake House North Bay, situated on a quiet dead-end drive on the North Bay of Lake Saint Catherine, offering incredible sunset views and large lake frontage on one of the best spots on LSC. With a lakeside sitting area and dock, large deck, horseshoes, fire pit, kayaks, and an expansive lawn, there is no shortage of ways to unwind and take in the serenity of this quintessential Vermont lake house, during every season. For more pics, follow us on IG @vtlakehouse_northbay

Guest favorite

Home in Poultney

4.93 out of 5 average rating, 300 reviews

Waterfront VT Lake House with Breathtaking Views!

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Guest favorite

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Guest favorite

Rental unit in Middletown Springs

4.89 out of 5 average rating, 236 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Guest favorite

Cottage in Whitehall

4.99 out of 5 average rating, 195 reviews

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Guest favorite

Home in Proctor

5 out of 5 average rating, 24 reviews

Peaceful Pond View ~30 mins to Killington

Relax with the whole family while taking in beautiful views of this peaceful pond. Kayak, fish and swim in the warmer months, or hit the slopes in the snow. There are also a few hiking trails within walking distance. Close to many restaurants and only half an hour away from Killington/Pico. Close to Chittenden, Lake Bomoseen & Lake George. Enjoy the quiet and get cozy while relaxing and spending quality time with each other. Small dogs considered, but must get owner approval.

Guest favorite

Cabin in Comstock

5 out of 5 average rating, 79 reviews

Cozy Country Cabin

NOVEMBER SPECIAL 10% off per night at this gorgeous cabin, tucked between the Green Mountains of Vermont and the gorgeous Adirondacks of NY. Soak up the morning sun on your private stone patio. Watch nature come to life on the pond and in the fields. Take a day trip to beautiful Lake George or Historic Saratoga Springs. For the winter season, there are many major ski resorts close by. The cabin has all new comfy furniture, mattresses, sheets, towels, comforters and blankets