Cottage vacation rentals in Western Massachusetts

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Top-rated cottage rentals in Western Massachusetts

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

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Guest favorite

Cottage in Craryville

4.91 out of 5 average rating, 524 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit and laundry facilities. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking

Guest favorite

Cottage in Lake George

4.92 out of 5 average rating, 131 reviews

Spacious Private Cottage in Beautiful Lake George.

This newly renovated cottage is located at the base of Prospect Mountain in a Family friendly neighborhood. 2 spacious decks, 6 Person Hot Tub (open year round), grill & outdoor fire pit. Private parking, walking distance to restaurants, bars, bike path, public beach, public docks and downtown. Approximately 1 mile to public boat launch. 10 minutes to West Mountain. 30 Minutes to Gore, and approximately 1 hour to Killington. 200 ft to Warren County snowmobile trail. Pack your bags & see you soon

Superhost

Cottage in Newbury

4.87 out of 5 average rating, 119 reviews

Country Cottage

Charming cottage with 3 bedrooms just a small walk to Sunapee lake. You can enjoy swimming off the dock or explore one of the many harbors on the lake. Mount Sunapee is just around the corner (2 minute drive) and offers many fun activities for the whole family. Including zip lines, mtn biking and much more. Sunapee State beach is also within walking distance or just a short drive away. Offers large sandy beach. This rustic cottage is a perfect place to make memories with family and friends.

Superhost

Cottage in Gardiner

4.9 out of 5 average rating, 161 reviews

Little Cottage Under the Ridge

Visit the cottage for an upscale retreat in the rock climbing epicenter of New York’s famous Shawangunk ridge. our mountain top paradise sits on a dead end road amongst untouched nature, only minutes to town, with a small chef’s kitchen, breakfast bar, and brand new everything. As the last property before Minnewaska’s protected preserve land, the cottage offers unmatched peace and quiet. Enjoy a private campfire beneath mature maple & oak trees that decorate our secluded five acre property.

Guest favorite

Cottage in Cornwall

4.93 out of 5 average rating, 147 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.

Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 123 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Guest favorite

Cottage in Saugerties

4.93 out of 5 average rating, 288 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Located on a bucolic country road on the border between Saugerties and Woodstock, this newly renovated 500 sq ft cottage is on a private acre filled with spaces to relax: screened in dining shed, fire pit, BBQ grill, a creek, forest & the magical sound of a hidden waterfall across the road. Just 10 min from Woodstock town square, 8 min to Levon Helm Studios, and 15 from Bearsville Theater, it's the perfect escape. (Pets welcome on a case by case basis. Please ask.)

Guest favorite

Cottage in Walden

4.96 out of 5 average rating, 108 reviews

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 119 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Superhost

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.

Top guest favorite

Cottage in Sturbridge

4.93 out of 5 average rating, 148 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Our petite (648 sq. ft.) lakeside cottage is the perfect place to unwind, relax and explore. Enjoy the spectacular unobstructed views of the sunset from the spacious deck (750 sq. ft.) from the comfort of your easy chair. The location of our cottage provides the tranquility of the lake, close to major routes and you will be minutes away from all that Sturbridge has to offer.

Guest favorite

Cottage in Copake Falls

4.91 out of 5 average rating, 353 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

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What guests are saying

Berkshires Cottage by Lake. Year Round Adventures.

4.95 out of 5 average rating, 273 reviews2 months ago

loved this cozy cabin for a snowed in weekend. the setting is beautiful and the house is completely stocked with everything you could need for quiet time with family. we came with two small kids and it was well suited for them. hoping to come back in the summer to enjoy the lake. thanks Scott for being such a phenomenal and responsive host amid the crazy snow storm.

Cottage in Becket

What guests are saying

Lakeside Cottage in Hope Valley, RI

4.98 out of 5 average rating, 138 reviews3 months ago

This was the ideal location for my husband and me to spend the holidays with our family who live across the lake. Will and John gave us a warm, friendly welcome and Quinn also checked in to make sure we settled in and had everything needed for a comfy cozy stay. It was easy to communicate with everyone and the location felt peaceful and private but not isolated. I can't imagine a more ideal experience and cannot thank Quinn enough for making this stay the best ever we've had with Airbnb!

Cottage in Hopkinton

What guests are saying

Charming Cottage Getaway

4.99 out of 5 average rating, 127 reviews3 months ago

This was our second time staying at the cottage. We had a wonderful stay over the holidays. The cottage was warm and cozy and Linda had tasteful and festive decor in every nook and cranny. We had the pleasure of meeting Linda. She is a truly wonderful person who loves what she does and it shines through in her beautiful property. So much attention to detail throughout the house. We hope to be back again soon!!

Cottage in New Paltz

What guests are saying

The Hickory Cottage - perfect!

4.76 out of 5 average rating, 623 reviews2 months ago

I had an absolutely fantastic stay at Judy and Eric’s cottage! The space was cozy, spotless, and had everything I needed for a comfortable getaway. But what truly made this experience special was their incredible hospitality. A snowstorm hit during my stay, and Judy and Eric went above and beyond by allowing me to stay extra time to ensure I was safe. Their kindness and generosity truly made a difference, and I couldn’t be more grateful. The cottage itself is peaceful and charming, with a breathtaking view into the woods that made for the perfect escape. Waking up to that scenery was one of the highlights of my stay! I highly recommend this place to anyone looking for a relaxing and welcoming retreat. Thank you, Judy and Eric—I will definitely be back!

Cottage in Accord

What guests are saying

Lakefront Lovely Cottage

4.83 out of 5 average rating, 47 reviews4 months ago

Brenda place was beautiful with a beautiful view especially when we work up to some light snow on the lake. The layout of the house was ideal for us with the big open living room and great updated kitchen. So many comfortable beds for us to use. Our favorite places were the sun room and dining rooms looking out at the lake, Brenda was was kind and helpful and adding a Christmas tree for us was a beautiful touch . Highly recommend, one of our best for sure, thank you

Cottage in Enfield

What guests are saying

The Cottage on Babbling Brook

4.95 out of 5 average rating, 196 reviews1 week ago

Super peaceful and tranquil! We were in town for the Gilmore Girls convention and absolutely loved our stay! Gorgeous surroundings and no noise even though you are right off the road. The creek outside was just beautiful and all the wood touches on the inside gave it that perfect "log cabin" feel. It was super clean and had all the amenities you could need. The wood burning stove was the cherry on top, making late night Netflix binges out of this world.

Cottage in New Milford

What guests are saying

Pond Cottage

4.97 out of 5 average rating, 150 reviews2 weeks ago

Had a wonderful time staying at Kim’s place — cozy, quaint, and did the job for our weekend getaway. It’s clear that she thinks of the little things, and we really felt like we were in someone else’s carefully curated space. A couple things to note: the heat was quite loud (and I’m a light sleeper), so we ended up turning it off at night. Probably less of an issue in the summertime! Similarly, we had the luck of being rained out most of our visit. The lighting in the cabin is a little precarious for those late nights or cloudy days. Lastly, and this may be partially operator error, but the blinds didn’t really offer a ton of privacy and appeared see-through at night. The location itself was peaceful and secluded, but it’s something to keep in mind if you prefer that extra privacy.

Cottage in Dorset

What guests are saying

Seasonal lake side cottage

4.94 out of 5 average rating, 282 reviews6 months ago

What can I say that hasn’t already been said. This place is a gem. We were the last to book for the year and Tim and Megan made sure that everything was perfect for when we got there. Upon arriving we immediately took the canoe on the lake and caught the last bits of sun. Although it rained for a good portion of our short trip there’s still something magical about having a cup of coffee on the back porch as the rain drops hit the water. 100 percent would come back. Thank you both for sharing this piece of paradise!

Cottage in Weare

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