Villa holiday rentals in Boys & Girls Club of the Berkshires Ice Rink

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

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The outdoor heated swimming pool is framed by a stone patio, with a shaded pergola alongside. Sunlight reflects off the clear water, capturing the serenity of the surrounding landscape and distant hills at sunset.

Villa in Coxsackie

4.87 out of 5 average rating, 70 reviews

5-BR Villa with Pool and Dog Friendly!

Welcome to Hudson View Villa! Relax with family or friends at a hilltop property overlooking The Hudson and Berkshires. Hudson View House offers over 2900 sq ft of gorgeous luxury space with views of the Hudson and Berkshires virtually from every room. The scenic views of the surroundings, breathtaking sunrises and sunsets will want you never to go home! Heated swimming pool now Open ( May - Sep/October). Propane grill on back deck overlooking Hudson River. Tesla charging- bring own adapter

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Top guest favourite

A contemporary living room features an 18-foot tall cathedral ceiling and a mix of stylish furnishings. Two couches are positioned around a circular blue rug, while a serene hammock hangs from the ceiling. A fireplace serves as the focal point, with plants adding life to the space.

Villa in Newburgh

5.0 out of 5 average rating, 95 reviews

Ultra Modern Private Oasis with River Views

Step into your brand new, ultra-modern secluded oasis with picturesque views of the Hudson River and Valley. The Balthus Haus was designed and built with sheer comfort, stylish aesthetics, and progressive functionality as the guiding tenets. Nestled high into the hillside the Haus maximizes 360 degrees of privacy and is surrounded by nature. Inviting and pleasant all year round with central AC and radiant heated floors throughout the living areas. Easily get away from NYC only 1.25 hours away!

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Guest favourite

A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.

Villa in Bloomingburg

4.87 out of 5 average rating, 117 reviews

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6-bedroom mountain villa, a peaceful retreat perfect for families and groups. Just about 1 hour from New York City, enjoy beautiful scenic views, comfortable living spaces, a well-equipped home, and plenty of outdoor space. Explore nearby hiking trails and local attractions, or simply relax and enjoy the quiet surroundings. Whether you're planning a family getaway or a weekend with friends, it's the perfect place to unwind, reconnect, and make lasting memories.

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Villa in Sharon

4.85 out of 5 average rating, 13 reviews

Beautiful Colonial Getaway with Private Pool

Come enjoy a country getaway in a rustic home dating to 1768! The colonial charm of this five-bedroom home is sure to capture your heart, offering a beautiful private pool , pool house, barn, and main house with plenty of space for the whole family or a group of friends. Situated on 22 acres of land in rural Connecticut, this home is perfect for a blissful retreat - located only two hours from NYC and three hours from Boston in a picturesque New England town. See notes for pool below.

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Superhost

A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.

Villa in Winhall

4.84 out of 5 average rating, 31 reviews

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

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Guest favourite

Villa in Niskayuna

4.93 out of 5 average rating, 43 reviews

The Mansion at Rebecca’s Fountain near Saratoga NY

The Mansion at Rebecca’s Fountain, a private hilltop estate overlooking the Mohawk River, marina, and surrounding mountains. Designed for travel & seasonal stays, is the top choice for business travelers, executives, & private groups. Ideally located near Saratoga Springs & the Racetrack, Lake George, Albany NY. 11-bed luxury retreat on 3 acres with pond, hot tub, outdoor amenities, and curated services including Private Hibachi Chef, catering, & in-home wellness. Experience more.

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Top guest favourite

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

4.95 out of 5 average rating, 100 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

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Top guest favourite

The villa's exterior showcases a large three-story structure, adorned with white siding and multiple windows. A spacious deck leads to the front entrance, framed by greenery from surrounding trees. The sky above is partly cloudy, providing a serene backdrop.

Villa in Stockbridge

4.96 out of 5 average rating, 67 reviews

Historic Stockbridge Villa on 25 acres

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop, a grand party or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

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Guest favourite

A bright living room features a comfortable seating area with a white sofa and chairs. A large artwork is mounted above a fireplace, while a decorative mirror is positioned nearby. Natural light enters through a large window, revealing expansive views outside.

Villa in Hudson

4.94 out of 5 average rating, 81 reviews

Mountain-View Retreat @ Hudson

Experience breathtaking mountain views from this designer-decorated home in the heart of Hudson.. Inside, enjoy a full game room, in-house laundry, and on-premise parking. The fenced property offers complete privacy with a security system. Walk to downtown Hudson (5 minutes drive), access nearby track and tennis courts, or take a short drive to Catskills trails, Bash Bish Falls, and Hunter Mountain. Ideal for relaxation and adventure, with easy Amtrak access nearby.

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Guest favourite

A game room features a pool table, shuffleboard table, and comfortable seating. Large windows allow natural light to fill the space, highlighting rich wood accents and green walls. Access to the outdoor area is provided through glass doors, complementing the recreational atmosphere.

Villa in Cornwallville

4.95 out of 5 average rating, 106 reviews

Catskills Retreat-Pool, Hottub, Bar, Shuffleboard

Welcome to Blue Heaven! A true paradise retreat with 2 houses, your own private inground pool, outdoor shower, pool house, playground, a Speakeasy bar room with billiards, darts, and shuffleboard! Located in the heart of the Catskills just 3 minutes away from Zoom Flume water park and 15-20 minutes away from Hunter/Windham Mountains. Enjoy swimming, roasting smores in the firepit, hiking, skiing/snowboarding, snowshoeing, or soaking up the stars in our hot tub.

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Top guest favourite

The historic estate features a grand facade highlighted by multiple gabled roofs and a striking red front door. Soft lighting glows from the windows, and lush greenery surrounds the stone steps leading to the entrance, emphasizing the peaceful atmosphere of the property.

Villa in Goshen

5.0 out of 5 average rating, 26 reviews

Goshen Historic Estate w/ Hot Tub near Legoland

Set among the rolling hills of Goshen, this historic estate blends rustic charm with a touch of luxury, creating a peaceful getaway from city life. Just 19 miles radius distance from West Point and minutes from Legoland, this beautifully preserved home places you at the center of the Hudson Valley’s best attractions. Be sure to check out the Brotherhood Winery, the oldest winery in America, for a memorable local experience!

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Guest favourite

Villa in Kerhonkson

4.96 out of 5 average rating, 356 reviews

Villa Retreat: Yoga Studio, Theater, EV Charger

Multi-level forest villa retreat in the Gunks, perfect for wellness escapes, creative retreats, or group getaways. Enjoy a private yoga studio, 110" home theater, EV charger, handmade furnishings, Casper and Nectar premium mattresses, and inspiring original art. Surrounded by forest with decks, private nooks, and cozy lounges, this beautifully designed home blends boutique comfort with spacious indoor-outdoor flow.

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