Vacation rentals in North Canaan

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Top-rated vacation rentals in North Canaan

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Guest favorite

A covered front porch features wooden flooring and is framed by dark columns. Two rustic wooden chairs are positioned beside a small table, creating a space for relaxation. Surrounding greenery is visible, enhancing the natural setting.

Apartment in Amenia

4.92 out of 5 average rating, 105 reviews

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Guest favorite

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

Chalet in Otis

4.94 out of 5 average rating, 417 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

Top guest favorite

Guesthouse in Millerton

4.98 out of 5 average rating, 104 reviews

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

Top guest favorite

Guest suite in Winchester

4.96 out of 5 average rating, 149 reviews

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom private bath suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. We follow all Airbnb policies & State of CT COVID cleaning guidelines. Please do not trespass on the property of private residences, across the street on the lake side. These are private residences. There are public beaches public access areas for your enjoyment.

Top guest favorite

A winter scene is depicted with a red building contrasting against a vibrant sunset sky, filled with shades of orange and pink. Snow covers the ground and rooftops. Dark trees frame the image, contributing to the serene atmosphere.

Apartment in Canaan

4.99 out of 5 average rating, 144 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 wooden bowl filled with various eggs sits on a wooden countertop next to a white microwave. A green ceramic pitcher filled with vibrant yellow daffodils adds a fresh touch to the space.

Apartment in Sheffield

5 out of 5 average rating, 366 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.

Guest favorite

A modern kitchen features white marble countertops and stainless steel appliances, including a gas stove and coffee maker. Skylights provide natural light, while open shelving showcases plants. Two black bar stools are positioned at the island, and a round dining table is visible in the foreground.

Cottage in Cornwall

4.92 out of 5 average rating, 155 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Superhost

A modern bathroom is featured, showcasing a walk-in shower with a glass enclosure. A sleek vanity with a dark wooden base holds a white sink. Above, a round mirror is mounted on the wall. Geometric floor tiles add visual interest, complemented by a black shower fixture.

Apartment in Millerton

4.79 out of 5 average rating, 108 reviews

The Studio

Millerton, NY is a weekenders dream! Enjoy a peaceful stay at our newly renovated Studio fully furnished and with a Queen Bed. You’re just a short walk from everything the village of Millerton has to offer! Grab a bite to eat at the popular Oakhurst Diner or indulge in a coffee at Irving Farm Coffee Roasters. After that, make your way to Westerlind to do a little shopping, pop into Oblong Books or enjoy the charm of an old time film theater by checking out The Movie house.

Guest favorite

Lush greenery surrounds a flowing river, with vibrant green leaves overhead and ferns lining the banks. The water can be seen gently moving over rocks, creating a peaceful natural setting in the woods.

Treehouse in New Marlborough

4.91 out of 5 average rating, 128 reviews

Double 3 Bedroom Tree House in the Berkshires

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.

Guest favorite

A well-appointed bathroom features a wooden vanity with a marble countertop and a round mirror above. Two neatly arranged white towels hang on a rack beside the sink, and a sleek toilet is positioned adjacent to a wastebasket on the floor.

Guesthouse in New Marlborough

4.9 out of 5 average rating, 199 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!

Top guest favorite

A wooden sauna is showcased with glass doors, highlighting a spacious interior with wooden benches and a soothing blue light. Natural light filters in through a window, adding warmth to the inviting atmosphere.

Farm stay in Ancram

4.96 out of 5 average rating, 335 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Top guest favorite

Treehouse in Wallkill

4.99 out of 5 average rating, 313 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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Other great vacation rentals in North Canaan

Guest favorite

A person stands in a grassy field surrounded by goats. The individual cradles an infant in a carrier while wearing a wide-brimmed hat. The goats are spread out across the field, grazing among the tall grasses and plants, with lush greenery in the background.

Tent in Canaan

4.97 out of 5 average rating, 29 reviews

glamping tent in hidden pasture

MichelleRating, 5 stars8 months ago

Marleen and Dan were incredibly friendly hosts who went above and beyond to make us feel comfortable. Their two sweet boys bonded with my kids, and they had a great time playing together. It was a bit cold during our stay; the wood-burning stove mentioned in older reviews is no longer usable. We stayed warm under cozy bedding but needed layers and hats at night. We enjoyed having a fire each night to cook dinner and spend quality time together disconnected. Just remember, you’re on a working farm—bring boots or proper shoes. I also wish I had brought some written directions since we couldn’t use GPS when leaving the tent, but there is WIFI available near the main house. Other highlights: We visited a nearby town for a fall festival that felt like an episode of Gilmore Girls, and my kids loved helping with the offered farm chores tour, interacting with the chickens, horses, ducks, and even petting bunnies!

Guest favorite

A flowing waterfall cascades over a stone structure, creating a serene water feature. Lush greenery lines the edges, while smooth stones are partially visible in the foreground. The sky is filled with soft clouds, adding a peaceful backdrop to the natural setting.

Home in Litchfield County

5 out of 5 average rating, 18 reviews

Blackberry River Retreat

DanielRating, 5 stars7 months ago

Meredith’s house is absolutely great. Spotlessly clean, comfy beds and living room, very spacious. It is adjacent to a very tranquil river and has a big back yard. Getting into the area was a bit difficult due to some serious roadwork, but once we were there, it was splendid. Meredith is super responsive and a great host. Would come back!

Guest favorite

Cabin in Becket

5 out of 5 average rating, 6 reviews

WALK to lake! Dog friendly, A-Frame in Berkshires!

FranciscoRating, 5 stars1 week ago

Beautiful little cabin, peacefully in the woods. Great, friendly, and responsive hosts. Perfect location to relax, walk around, find closeby hikes and hidden gems, including some great breakfast spots. 10/10 would recommend.

Top guest favorite

Home in Salisbury

5 out of 5 average rating, 49 reviews

Greystone at Twin Lakes

GingerRating, 5 stars1 month ago

You’ll have everything you need in this cozy home—John has truly thought of everything to make your stay comfortable. I really appreciated the little extras, like coffee and essential condiments. It’s those thoughtful touches that make a trip feel so much easier and more enjoyable. Big thanks to John and the hosting team for creating such a warm and welcoming space. Also, thanks, John, for being super responsive—he quickly mailed me some things I accidentally left behind. So grateful for that! Thank you again!

Top guest favorite

Cabin in Saugerties

5 out of 5 average rating, 38 reviews

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars4 days ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

Guest favorite

A charming white house with a spacious front porch, featuring multiple seating areas. A row of adirondack chairs is positioned on the well-maintained lawn, surrounded by neatly trimmed shrubs. The clear blue sky adds to the inviting landscape, creating a welcoming outdoor environment.

Home in Salisbury

4.93 out of 5 average rating, 15 reviews

Stylish getaway in the Berkshires

NedRating, 5 stars2 weeks ago

Bright, light good layout inside and short walk to Salisbury and very short drive to Lakeville. Would definitely stay here again

Top guest favorite

A stack of firewood is positioned beside a pickup truck parked in a grassy area. The truck's bed is open, indicating it's ready for transport. In the background, a clear blue sky and distant tree line are visible, enhancing the rural setting.

Home in Millerton

4.99 out of 5 average rating, 68 reviews

1800s Schoolhouse with Modern Amenities

MattRating, 5 stars2 weeks ago

Cathy was extremely helpful and great with communicating clear instructions for our stay at her great home!

Top guest favorite

A vibrant garden area is filled with blooming purple and white irises, complemented by yellow flowers. Lush green foliage surrounds the flower beds, with distant trees and a natural landscape visible in the background. The scene includes a subtle pathway leading through the floral arrangement.

Guest suite in Sheffield

5 out of 5 average rating, 79 reviews

The Sunset Suite~Great South Berkshire Location!

MaureenRating, 5 stars2 days ago

Sharon and Oliver were wonderful hosts! They greeted me with friendly smiles and a gift of maple syrup upon arrival, and they were proactive and responsive throughout my stay. The apartment is spacious, spotless and inviting, and I immediately felt right at home. The super comfy bed and blackout shades make for a great night's sleep, and the view from the windows is spectacular. This airbnb was one of my favorites, and I look forward to staying here again when I come back to the area.

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Vacation rentals in North Canaan

Top-rated vacation rentals in North Canaan

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