Places to stay in Canaan

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Canaan

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Old Chatham

4.96 out of 5 average rating, 25 reviews

Post and Beam Hilltop Sanctuary

CatherineRating, 5 stars3 months ago

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

Guest favorite

Apartment in Stockbridge

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

ReganRating, 5 stars3 months ago

Theresa’s beautiful Norman Rockwell studio was so much better than I could have imagined! She was so thoughtful from start to finish with clear and easy communication about everything. Parking was very easy and you will clearly have a space right behind the building. The large picture window in the middle of the living room with a Christmas tree in the center was so lovely and heart warming! Very quiet yet steps from shopping and restaurants (the best breakfast in town can be had at Main Street Cafe downstairs!) I would highly recommend this charming apartment for anyone wanting a charming experience in Stockbridge. 10 out of 10!

Superhost

Apartment in Kingston

4.77 out of 5 average rating, 115 reviews

In the Heart of Kingston

ElizabethRating, 5 stars1 week ago

Carin's apartment was cozy and clean, a perfect place to rest after your adventures. It is very close to the train tracks and there were complimentary ear plugs on the bedside table, if you need them. The sound of the train did not bother us at all but we are very used to it. Carin was very responsive when we had questions. I highly recommend Carin's place for your stay in Kingston!

Guest favorite

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

FeliciaRating, 5 stars2 months ago

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

Top guest favorite

Guesthouse in Bethel

5 out of 5 average rating, 16 reviews

Tranquil getaway cottage in charming neighborhood

MelRating, 5 stars5 days ago

Erika’s cozy cottage was the perfect getaway. It was in such a beautiful and peaceful neighborhood. The cottage was very nice inside, private and it matched the description. Erika was also a very friendly and attentive host. Would recommend this place to others. 10/10 !!!

Guest favorite

Farm stay in Kent

4.87 out of 5 average rating, 310 reviews

(°) The Wandering Peacock (°)

AlyssaRating, 5 stars4 days ago

I went for my boyfriends 25th birthday it was absolutely stunning from all of the art everywhere in the house and outside! We stayed in the sauna from when we got there till late at night it was an absolutely wonderful experience even just for a night!

Top guest favorite

Guest suite in Newburgh

4.92 out of 5 average rating, 168 reviews

Cozy Country Efficency in Hudson Valley

JulianneRating, 5 stars4 months ago

The space was great! It was big enough for two and decorated very nicely. The space had everything you needed, including some toiletries and misc items (iron, tea kettle, etc) which made the stay even better. Thank you!!

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

JulietteRating, 5 stars6 months ago

We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!

Top guest favorite

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

MichelleRating, 5 stars2 months ago

Lockwood Lodge is a beautiful and peaceful place in a perfect location. Our families loved watching the snow come down from the big windows, the view is spectacular. Our kids loved the vintage video game consoles, the grownups loved the records and games/puzzles, and we all felt right at home in the lovely house. It was a perfect spot to hunker down in the snow storm. Jeremy was incredibly responsive and thoughtful and did much to make sure our stay was perfect. We hope to visit again in the summer to take advantage of the pool, which must be really special against the backdrop of that view.

Guest favorite

Home in Tannersville

5 out of 5 average rating, 44 reviews

Luxury Custom Home With Hot Tub Minutes From Town

MarissaRating, 5 stars2 months ago

One of the best homes we’ve stayed in on Airbnb! Had everything you could ask for and more. We visited for a ski trip and unfortunately conditions were not great, but still had an amazing trip because of the home! Highly recommend.

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What guests are saying

Heart of Catskills:Pond Views,Backyard Dining+BBQ.

4.95 out of 5 average rating, 20 reviews4 days ago

Came back for another lovely stay! This is the perfect location for outdoor activities and still close to our favs like Hudson & Woodstock. House had everything we needed to stay with two young kids and the backyard can’t be beat! Host is fast to reply and accommodating. Would absolutely recommend!

Home in Round Top

What guests are saying

Garden Retreat Theme

4.8 out of 5 average rating, 108 reviews2 months ago

Everything about this place was wonderful. It was centrally located to Poughkeepsie and was with 15 minutes of everything we hoped to do. The apartment was very clean, well stocked, and private with lots of homey touches that made it extra comfortable. We particularly loved the robes that were provided and the comfortable king sized bed. Delia was extremely responsive and proactive in communicating with us prior to and during our stay. We highly recommend this place for a cozy getaway in the Hudson Valley.

Home in Poughkeepsie

What guests are saying

The Serendipity Spot

4.95 out of 5 average rating, 40 reviews2 months ago

Their place was perfect for a couples weekend getaway. It was very clean, convenient, and we loved our stay there. The overall location and the town itself were perfect for our romantic ski weekend plans. Andrew and Susanne were very kind and inviting and were excellent hosts!

Guest suite in Great Barrington

What guests are saying

Creekside Cottage Retreat: Light, Cozy, Getaway

4.92 out of 5 average rating, 24 reviews6 months ago

Cooper’s airbnb was excellent for the price. It was quiet, clean and cozy. Not the most updated home, but again great for the price. Amazing location. Centrally located and had a gorgeous yard and backyard creek. Cooper was very responsive and helpful! Highly suggest for a casual trip (:

Cottage in Saugerties

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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 places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Canaan's top sights

Falls Village Inn21 locals recommend

Mountainside Cafe19 locals recommend

Music Mountain11 locals recommend

Beckley Iron Furnace State Park8 locals recommend

Great Falls connecticut7 locals recommend

Land of Nod Vineyard and Winery6 locals recommend

Other great vacation rentals in Canaan

Top guest favorite

Home in Athens

5 out of 5 average rating, 38 reviews

Perfect home for a getaway from NYC

ScottRating, 5 stars3 weeks ago

Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!

Top guest favorite

Home in Millerton

4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago

We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!

Superhost

Home in Litchfield County

4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

JadeRating, 5 stars2 months ago

We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!

Guest favorite

Home in Cornwallville

4.92 out of 5 average rating, 50 reviews

Catskill/Windham Gorgeous Home

SwetaRating, 5 stars2 months ago

Stan is an amazing host and was so courteous that he cleaned up the drive way when it snowed like crazy. He was extremely warm and nice to our daughter and it was great experience. We enjoyed the house and hospitality.

Top guest favorite

Home in Great Barrington

5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago

We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!

Top guest favorite

Home in Great Barrington

5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

AnnieRating, 5 stars3 months ago

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

Guest favorite

Home in Woodstock

4.92 out of 5 average rating, 468 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

SeanRating, 5 stars2 weeks ago

Unique space minutes form downtown Woodstock. The home offers peace and quiet to unwind from modern hectic life. Tune into focused intentional living. Records, wood fires, and sauna all help to create a retreat that’s sure to recharge and inspire. Lovely hosts!

Top guest favorite