Vacation rentals in North Canaan

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Top-rated vacation rentals in North Canaan

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Guest favorite

A charming white house with green shutters features a spacious front porch, surrounded by trees. Large windows allow natural light to fill the interior. A stone bench and potted plants provide a welcoming entryway, inviting relaxation in the tranquil outdoor setting.

Cottage in Canaan

4.85 out of 5 average rating, 177 reviews

Cozy Little Cottage

Small comfortable place close to Lime Rock Park and Ski Butternut. It has 3 available bedrooms including one master with full bath. Lots of great restaurants in the area and places to hike or take out your canoe or kayak. Nice private backyard. There is a small fish pool to enjoy. I do have cameras pointing at the front door and back door to see when guests arrive and when they leave. Please don't try and sneak in extra guests you didn't intend to pay for. I've has these issues before. Welcome!

Top guest favorite

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

4.99 out of 5 average rating, 225 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

Guest favorite

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

4.95 out of 5 average rating, 427 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favorite

A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.

Apartment in Copake Falls

4.91 out of 5 average rating, 344 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Top guest favorite

A secluded mid-century cabin with a warm red exterior is surrounded by lush greenery and trees. A gently flowing brook with smooth stones runs past the cabin, providing a serene atmosphere in this tranquil natural setting.

Cabin in Norfolk

4.99 out of 5 average rating, 101 reviews

The Red Cabin-Secluded Getaway with backyard Brook

Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

Guest favorite

A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.

Cottage in Sheffield

4.94 out of 5 average rating, 156 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Top guest favorite

The exterior of a two-story house is displayed, featuring a combination of white siding and a metal roof. An American flag hangs from the porch, surrounded by greenery and flower beds. The front pathway leads to a welcoming porch space.

Apartment in Canaan

4.99 out of 5 average rating, 151 reviews

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Top guest favorite

A spacious living area features comfortable seating, a glass coffee table, and a dining space with wooden chairs. The kitchen is visible, showcasing modern appliances and a light wood countertop. Natural light illuminates the room, creating a warm and open atmosphere.

Apartment in Sheffield

5 out of 5 average rating, 373 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Top guest favorite

A cozy living room features a large sectional sofa and an ornate ottoman at the center. A spacious TV unit stands against the far wall, complemented by natural light filtering through multiple windows. A bookshelf and decorative pieces enhance the inviting atmosphere.

Guest suite in Canaan

4.98 out of 5 average rating, 360 reviews

Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Guest favorite

A large window frames a serene forest view, revealing lush greenery and tall trees. Soft bedding in shades of gray is neatly arranged on the spacious bed, creating a tranquil atmosphere that connects the indoors to the surrounding nature.

Tiny home in New Marlborough

4.93 out of 5 average rating, 105 reviews

Cozy Riverside Tiny House & Wood Sauna

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, an outdoor shower, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Top guest favorite

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

4.99 out of 5 average rating, 117 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Guest favorite

A loft-style bedroom is visible, featuring a spacious bed with white linens. Two windows allow natural light to brighten the room, complemented by a modern ceiling fan. A decorative lantern hangs above, and a wood-paneled railing leads down to the staircase.

Guesthouse in New Marlborough

4.91 out of 5 average rating, 202 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!