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Waterfront vacation rentals in Boys & Girls Club of the Berkshires Ice Rink

Find and book unique waterfront rentals on Airbnb

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

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

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Guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.94 out of 5 average rating, 142 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Guest favorite
A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.
Home in Mount Tremper
4.93 out of 5 average rating, 265 reviews

Mt. Wonder: Big Cozy Cabin with Wow View

Welcome to Mt Wonder. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Ten min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2br 1ba cabin, cozy and spacious, with a unique magical feel. Mega amenities incl the tub, BBQ, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin cabin: "Wonders Never Cease"

Top guest favorite
A modern A-frame cabin is illuminated under the evening sky, featuring large glass doors that open to a spacious deck with outdoor seating. The surrounding wooded area is visible, adding to the tranquil setting of the nature retreat.
Cabin in Freehold
4.94 out of 5 average rating, 339 reviews

Tiny Home A-Frame with Hot Tub & Creek

Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our brand new home has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to WFH.

Top guest favorite
A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.
Home in Catskill
4.95 out of 5 average rating, 248 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Guest favorite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford
4.95 out of 5 average rating, 242 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favorite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket
5 out of 5 average rating, 107 reviews

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Guest favorite
A modern bedroom features a plush King-sized bed with crisp white linens and decorative pillows. A door opens to an outdoor area, while a unique wall design adds architectural interest. A small console table with a coffee maker is positioned against the wall.
Apartment in Great Barrington
4.95 out of 5 average rating, 177 reviews

King Bed, Wi-Fi, 2m Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Smart TV

Guest favorite
The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.
Treehouse in New Marlborough
4.9 out of 5 average rating, 157 reviews

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Top guest favorite
Home in East Jewett
4.99 out of 5 average rating, 137 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Top guest favorite
The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.
Treehouse in Willow
4.96 out of 5 average rating, 862 reviews

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Top guest favorite
The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.
Cottage in Pawling
4.99 out of 5 average rating, 175 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favorite
An inviting living space features a modern wood stove as its focal point. Large windows allow natural light to fill the room, revealing views of the surrounding trees. Two comfortable sofas are arranged for relaxation, with a hanging planter adding a touch of greenery.
Cabin in Ancram
5 out of 5 average rating, 158 reviews

The Ancram A - Luxury Mid-Century Modern Cabin

Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.

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