Holiday rentals in Canaan

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Top-rated holiday rentals in Canaan

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Guest favourite

Home in Canaan

5.0 out of 5 average rating, 133 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

26 Jan – 2 Feb

€ 147 per night

Guest favourite

Flat in Canaan

4.98 out of 5 average rating, 103 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.

17–24 Jun

€ 141 per night

Superhost

Cottage in Canaan

4.9 out of 5 average rating, 126 reviews

Plan your Berkshires by the lake

Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. There is also a pullout queen size couch. Perfect for families. Hi-speed Spectrum internet, AllClad cookware, electric range, microwave, sharp knives, coffee maker, charcoal BBQ, and tons of places to hike. Apple TV and a Bose Bluetooth soundbar. There is also a large Solo Stove firepit as well as 2 kayaks and a paddle board for tooling around the lake. Close to supermarkets. 15 minutes to Tanglewood!

24 Sep – 1 Oct

€ 260 per night

Guest favourite

Cabin in Canaan

4.99 out of 5 average rating, 231 reviews

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

4–11 Oct

€ 167 per night

Guest favourite

Home in Canaan

4.9 out of 5 average rating, 150 reviews

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

15–22 Dec

€ 299 per night

Guest favourite

Guest suite in Canaan

4.98 out of 5 average rating, 293 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!!!

21–28 Nov

€ 158 per night

Guest favourite

Guest suite in Valatie

4.98 out of 5 average rating, 230 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

27 Sep – 4 Oct

€ 94 per night

Guest favourite

Home in Chatham

4.9 out of 5 average rating, 144 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to fine dining & Main St pubs/pizza/movies/shopping. 12mi Hudson Amtrak (taxi, Uber avail). Walk to town park w/swim pond. 30mins Albany/Lenox. Keyless entry. Hosts a text away if needed. Smoke/Pet-free property. Check-in 4pm/-out 11a. 55" Sony Roku TV. Reliable high-speed WiFi. Stocked kitchen/full bath incl W/D. Private outdoor dining area w/propane bbq. 2 guests max preferred, a 3rd could be accommodated at extra charge.

11–18 Oct

€ 123 per night

Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

18–25 Jul

€ 165 per night

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

26 Nov – 3 Dec

€ 84 per night

Guest favourite

Home in New Lebanon

4.99 out of 5 average rating, 348 reviews

The old sawmill from 1771

The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.

5–12 Mar

€ 147 per night

Guest favourite

Cabin in Canaan

4.98 out of 5 average rating, 132 reviews

Newly Renovated Cabin in the Country

The Heartwood Cabin is a freshly renovated rustic retreat nestled in the sleepy hamlet of Red Rock, NY. We just lovingly rebuilt and redecorated this charming cabin as a family getaway —we set out to create a place where we would be proud to bring our family and friends.

14–21 Sep

€ 336 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Canaan holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Canaan

Guest favourite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

19–26 Aug

€ 95 per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 180 reviews

Tiny House on 70 Private Acres in Hudson Valley

6–13 Aug

€ 156 per night

Guest favourite

Farm stay in New Lebanon

4.95 out of 5 average rating, 184 reviews

Barn Stay at Shadowbrook Farm

28 May – 4 Jun

€ 215 per night

Guest favourite

Guest suite in Lenox

4.96 out of 5 average rating, 168 reviews

T’Other House

9–16 Sep

€ 168 per night

Guest favourite

Loft in East Nassau

4.99 out of 5 average rating, 151 reviews

Dog Friendly Farm Spring bird watching

15–22 Sep

€ 167 per night

Guest favourite

Flat in Canaan

5.0 out of 5 average rating, 83 reviews

Mountain View Getaway

13–20 Sep

€ 111 per night

Guest favourite

Home in Canaan

5.0 out of 5 average rating, 13 reviews

Private Retreat! Hot Tub, Pool Table & Movie Room

25 Sep – 2 Oct

€ 285 per night

Guest favourite

Flat in East Chatham

4.91 out of 5 average rating, 44 reviews

Bennett Abode

24–31 Dec

€ 103 per night

Show all

Quick stats about holiday rentals in Canaan

Total rentals
20 properties
Local attractions
United States Postal Service, Sandy Klempner Antiques & Interiors and Stoddard Field
Popular amenities
Gym, BBQ grill and Laptop-friendly workspace
Wifi availability
20 properties include access to wifi
Total number of reviews
560 reviews
Nightly prices starting at
€ 38 before taxes and fees

Holiday rentals in Canaan

Top-rated holiday rentals in Canaan

Home in Canaan

Flat in Canaan

Cottage in Canaan

Cabin in Canaan

Home in Canaan

Guest suite in Canaan

Guest suite in Valatie

Home in Chatham

Farm stay in Pittsfield

Guest suite in Austerlitz

Home in New Lebanon

Cabin in Canaan

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Canaan holiday rentals

Other great holiday rentals in Canaan

Guest suite in Hancock

Tiny home in Chatham

Farm stay in New Lebanon

Guest suite in Lenox

Loft in East Nassau

Flat in Canaan

Home in Canaan

Flat in East Chatham

Quick stats about holiday rentals in Canaan

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore