We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Canaan

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Canaan

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest suite in Richmond

4.93 out of 5 average rating, 181 reviews

Ski Bousquet/Private Ranch/Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

Rental unit in Canaan

4.98 out of 5 average rating, 126 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.

Rental unit in Canaan

4.99 out of 5 average rating, 144 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest suite in Canaan

4.98 out of 5 average rating, 327 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!!!

Home in Canaan

4.91 out of 5 average rating, 161 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.

Cabin in Canaan

4.99 out of 5 average rating, 247 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.

Guesthouse in Lenox

4.92 out of 5 average rating, 194 reviews

Modern Barn with Loft at House on Golden Hill

Featuring 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

Farm stay in Pittsfield

4.99 out of 5 average rating, 168 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 just relax out on the balcony and take in the views.

Tiny home in Chatham

4.99 out of 5 average rating, 215 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Home in Chatham

4.98 out of 5 average rating, 106 reviews

Hilltop studio apartment on 100 acres near village

Large newly restored studio apartment attached to a single family home nestled in a quiet pastoral setting just outside the Village of Chatham, NY. Your private entrance leads to a bright 20' X 40' room, and includes a full bathroom, kitchen (no cooktop or oven) with a 2nd floor view of the countryside. The host lives full time in the main house.

Home in New Lebanon

4.99 out of 5 average rating, 360 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.

Cabin in Canaan

4.97 out of 5 average rating, 149 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Canaan vacation rentals

Free parking on premises

Air conditioning

Stay near Canaan's top sights

United States Postal Service6 locals recommend

Backwater Grille6 locals recommend

Canaan General Store3 locals recommend

Other great vacation rentals in Canaan

Home in Canaan

4.96 out of 5 average rating, 72 reviews

Peaceful Berkshire Getaway (A/C, Lake Access)

Home in Old Chatham

4.97 out of 5 average rating, 35 reviews

The Red House

Home in Canaan

4.99 out of 5 average rating, 83 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

Cabin in East Nassau

5 out of 5 average rating, 22 reviews

Luxury Cabin With Colorful Views for Fall Folliage

Home in Canaan

4.89 out of 5 average rating, 79 reviews

Quiet Lakeside Cabin on Private Road

Cottage in Chatham

5 out of 5 average rating, 24 reviews

Guesthouse 505

Home in Old Chatham

4.96 out of 5 average rating, 23 reviews

Post and Beam Hilltop Sanctuary

Home in East Chatham

4.98 out of 5 average rating, 65 reviews

Relaxing Retreat-Enjoy Hudson Valley & Berkshires

Quick stats about vacation rentals in Canaan

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
720 reviews
Wifi availability
20 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Local attractions
United States Postal Service, Sandy Klempner Antiques & Interiors, and Stoddard Field

Frequently Asked Questions

Do bed and breakfast rentals in Canaan have wireless internet?
Absolutely! We offer over 10 bed and breakfast rentals with wireless internet in Canaan. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Canaan have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Canaan. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in bed and breakfast rentals in Canaan?
Experience the best of Canaan with our bed and breakfast rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Bed And Breakfast Rentals in Canaan?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore