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Holiday houses in Connecticut River

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Top-rated holiday rentals in Connecticut River

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Top Guest favourite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
5 out of 5 average rating, 104 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Top Guest favourite
An open living area features a spacious sectional sofa adorned with various throw pillows. A large bed is positioned nearby, with a wooden partition offering privacy. Industrial-style light fixtures hang from the high ceiling, and a fully equipped kitchen is visible in the background.
Cabin in Stoddard
4.99 out of 5 average rating, 138 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Top Guest favourite
A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 233 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top Guest favourite
Place to stay in Shapleigh
5 out of 5 average rating, 113 reviews

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

Top Guest favourite
An inviting interior showcases rustic wood paneling and a unique round window with leafy views. A small dining table is set near the window, while a staircase leads to an upper area. Natural light enhances the warm atmosphere within the space.
Home in Campton
4.96 out of 5 average rating, 103 reviews

Log Cabin on the River w/ Private Hot Tub

This log cabin tiny home is located right in Campton Village. It is clean, and very bright and cheery thanks to the floor-to-ceiling window that overlooks the Mad River. Includes a SMALL kitchenette (not recommended for those serious about cooking nightly feasts) and a locked outdoor storage space for skis and outdoor equipment. Small 2-person hot tub. WiFi. Level 2 EV charger on site (extra fees apply). 5 min walk from a craft brewhouse, grocery store, a vintage arcade and candy store.

Top Guest favourite
Barn in Chester
4.99 out of 5 average rating, 732 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Top Guest favourite
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro
4.94 out of 5 average rating, 616 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Top Guest favourite
Loft in Peterborough
4.96 out of 5 average rating, 307 reviews

1850 Waterfall Mill-Loft Style Chic

IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

Top Guest favourite
A spacious living area features a vaulted ceiling with wooden beams. Large windows allow natural light to fill the room, offering a glimpse of Lake Sunapee outside. Comfortable seating arrangements include a dark blue sofa and light-colored poufs, complemented by a decorative mural on the wall.
Home in Sunapee
4.98 out of 5 average rating, 227 reviews

@SunapeeSeasons—Across from Dewey Beach, Lake View

Welcome to 'Sunapee Seasons'—overlooking Dewey Beach on Lake Sunapee and 8 minutes from Mount Sunapee, with each theme bedroom celebrating one iconic season in this ever-changing region. Let in the breeze and unwind indoors ...or simply walk to the sand beach across the street. In winter Mt. Sunapee is just up the road, and come fall the entire property is bathed in foliage. Once you've seen one "Sunapee season" we know you'll want to experience them all!

Guest favourite
A narrow dirt path winds through a lush landscape, leading to a charming tiny house nestled among greenery. Dappled sunlight filters through surrounding trees, highlighting the house's facade and inviting entrance.
Tiny home in Mansonville
4.92 out of 5 average rating, 516 reviews

Charming Tiny House bord de l'eau

Discover our charming Tiny House, ideal for a warm stay by the river. Enjoy on-site trails and private access to the water. This lovingly designed project reflects our happiness to have a peaceful haven where you can recharge your batteries and enjoy outdoor activities. We want to share this experience with those looking for a pleasant moment of well-being in the countryside. Treat yourself to a moment of serenity, alone or in love, in our little cocoon.

Top Guest favourite
Cabin in Newfane
4.99 out of 5 average rating, 302 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Top Guest favourite
A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.
Condo in Ludlow
4.93 out of 5 average rating, 167 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

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