Holiday rentals with a kayak in Boys & Girls Club of the Berkshires Ice Rink

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Top-rated rentals with kayak in Boys & Girls Club of the Berkshires Ice Rink

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Top guest favourite
Cabin in Lanesville
4.94 out of 5 average rating, 279 reviews

Only Ski In Out on Mtn| Hike, Golf, Fish, Recharge

Slopeside 1BR cabin sleeps 4! Step right onto Hunter Mountain from your porch or drive 5 min to scenic hiking trails. Prime location near the charming, colorful village of Tannersville. Enjoy a fully stocked kitchen & bath, high-speed WiFi, and an entertainment system with Netflix & all your other favorite streaming! Stay longer with the convenience of a W/D & dishwasher. Cozy up by the fireplace, take in the mountain views, or explore nearby dining, breweries, and outdoor adventures year-round!

Top guest favourite
Cabin in Bethlehem
4.94 out of 5 average rating, 105 reviews

Cozy Cabin, Fireplace, Ski Nearby

Escape to Deer Ridge Cabin, a serene & cozy retreat designed to help you unwind. Relax by the warm glow of the fireplace or venture out to enjoy nearby skiing & tubing at Mohawk Mt. and Mt. Southington. Explore scenic hiking trails, indulge in local wineries, or visit Litchfield just 10 minutes away for fantastic dining & boutique shopping. Located only 2 hours from NYC, this peaceful cabin offers the perfect winter escape to nature while keeping you close to it all. Your perfect getaway awaits!

Top guest favourite
A rustic cabin is visible in a snowy landscape, surrounded by tall trees and a wooden fence. The cabin is partially obscured by falling snowflakes, creating a serene and tranquil winter scene. Soft snow covers the ground and branches, enhancing the winter atmosphere.
Cabin in Colebrook
4.95 out of 5 average rating, 113 reviews

Rustic Pond Cabin: Nature, Stars & Serenity

Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!

Top guest favourite
An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.
Home in Great Barrington
4.96 out of 5 average rating, 187 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Top guest favourite
A scenic view of Lake Garfield is framed by lush trees, showcasing a still water surface reflecting the sky. Rolling mountains can be seen in the background, with hints of autumn foliage adding warmth to the landscape under a partly cloudy sky.
Home in Monterey
4.89 out of 5 average rating, 118 reviews

Hilltop Retreat w Magic View! 15 min Ski Butternut

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

Guest favourite
Cabin in Ferndale
4.93 out of 5 average rating, 259 reviews

Cozy Lakefront Catskills Cabin—2hrs from NYC!

This beautiful lakefront cabin is located at the end of a peaceful road adorned with tire swings and wildflowers. It is situated in a private community on a SMALL 3 acre lake, offering the perfect setting to enjoy morning coffee on the dock, taking refreshing afternoon swims in the lake, going for evening kayaking rides, and stargazing. You can unwind in our hammock nestled amidst the ferns next to a tranquil stream. We offer 2 kayaks and 1 SUP for your enjoyment. Best of all, 2 hrs from NYC.

Guest favourite
A dark mug rests beside a glass coffee maker on top of vintage books. Outside the window, a snowy forest scene is visible, enhancing the cozy ambiance of the indoor setting.
Cottage in Copake
4.91 out of 5 average rating, 113 reviews

Modern Mid-Century Cottage - Skiing @ Catamount

Let all your worries fade away in this beautifully remodeled modern cottage! Our 3 bedroom, 2 bath can sleep 8 adults in 2 Queen Beds, 2 Twin Beds and a Queen Sleeper Sofa. Relax by the fire pit out back or take out our 2 two person Kayaks and enjoy the lake in the summer, visit Catamount Ski Resort or other nearby ski mountains in the winter. The large, custom dinner table seats 8 comfortably with lots of room to hang, play games, watch movies and more. Guests must be 25 years old to rent.

Guest favourite
A firepit area is surrounded by several light blue chairs, set on a pebbled ground. The calm lake reflects the trees and landscape, creating a serene outdoor space ideal for gathering and relaxation.
Cottage in Becket
4.93 out of 5 average rating, 257 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Guest favourite
An open-concept living area features wooden ceilings and a bamboo floor. A sectional sofa and coffee table are positioned beside a dining table for four. Sliding glass doors provide access to an outdoor space, while large windows allow natural light to fill the cozy atmosphere.
Cottage in Bethlehem
4.99 out of 5 average rating, 142 reviews

Cozy Getaway | Pet Friendly | Amazing Location

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Guest favourite
A waterfront home is shown from an elevated view, featuring an expansive deck with outdoor seating and a gazebo. Colorful kayaks are positioned along the water's edge, with lush trees showcasing autumn foliage in the background, contributing to the serene atmosphere.
Home in Saugerties
4.94 out of 5 average rating, 198 reviews

Waterfront Three bedroom in Saugerties w/ Hot Tub

Welcome to a waterside haven! So peaceful, yet only a mile from the center of Saugerties. You will love this open concept, three bedroom, two full bath, waterfront home with year round outdoor Hot Tub! Swim, kayak, paddle board, fish, relax, BBQ all from your huge front deck. Private, peaceful, quiet on a dead end street. Near hiking, fall foliage, skiing, shops and all the Catskills has to offer. The house is family and dog friendly. See our social media Insta @esopuscreekhouse

Top guest favourite
A spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.
Cabin in Monterey
4.95 out of 5 average rating, 294 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 424 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

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