Holiday rentals in Colrain

4.87 out of 5 average rating, 438 reviews

Big, sunny 1893 flat steps from Bridge of Flowers

Urban 3-room (2 bdrm) apartment on 3rd floor of funky older apt building on the main street of Shelburne Falls. Apartment faces the street, with views of the hills beyond. New kitchen appliances, and newly remodeled bath with custom shower, tile floor, and washer/dryer. Interesting art throughout the apartment, including some original pieces. Steps to the Glacial Potholes, Bridge of Flowers; and all the galleries, shops, restaurants, and cafes that this charming New England village has to offer.

Guest suite in Greenfield

4.95 out of 5 average rating, 194 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

4.96 out of 5 average rating, 343 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

4.97 out of 5 average rating, 559 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Campervan/Motorhome in Guilford

4.93 out of 5 average rating, 139 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

4.99 out of 5 average rating, 143 reviews

Treehouse in Guilford

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Guest suite in Charlemont

4.91 out of 5 average rating, 209 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

4.99 out of 5 average rating, 137 reviews

Cabin in Guilford

Rustically Romantic Cabin Near Sweet Pond

COUPLES RETREAT, SOLO ESCAPES & WRITER'S DREAM in Southern Vermont - No Cleaning Fee Perfect for ENGAGEMENTS, HONEYMOONS & ANNIVERSARIES Authentic log cabin tucked into a private wooded cove outside of Brattleboro. A short tranquil walk to Sweet Pond State Park. Biking galore and Kayaking nearby. A variety of hikes to choose from. ROMANCE SPECIAL Stay 4-nights or more & receive hard cider, cheese & chocolate. Ask Me About ELOPEMENT & VOW RENEWAL CEREMONIES

4.95 out of 5 average rating, 191 reviews

Home in Colrain

Western Mass Getaway |AirHockey |HotTub |Firepit

Enter into the brightly lit kitchen/dining with seating for 10 while the kids enjoy the air hockey table and board games close by. You'll adore cooking in our stunning kitchen which guests absolutely love! The first floor bedroom is tucked away from the fun activities, while 4 bedrooms upstairs offer plenty of space and privacy. 5 minutes from Shelburne Falls and local areas for downhill and x-country skiing, hiking, restaurants, shops and more. Don't miss out!

4.95 out of 5 average rating, 165 reviews

Flat in Conway

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

4.95 out of 5 average rating, 169 reviews

Cabin in Guilford

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

4.96 out of 5 average rating, 409 reviews

Flat in Greenfield

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, safe neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

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Other great holiday rentals in Colrain

5 out of 5 average rating, 22 reviews

Guest suite in Colrain

Cozy elegant suite between Deerfield/NMH/Shelburne

MarianneRating, 5 stars3 weeks ago

Roxanne’s home is absolutely beautiful and peaceful. We were in the area for college graduation and as a result, our only regret is that we did not have more free time to spend at this tucked away oasis… we would love to visit again! We highly recommend Roxanne’s home for anyone looking to enjoy quiet, some local trails, and to take in nature. The suite is beautifully decorated and so inviting. I wanted to sit outside with a book and enjoy the surroundings. Roxanne baked us hot bread that was beyond delicious and made us feel like we were on vacation and being cared for. I hope we go back one day. I have a friend in mind who is a huge hiker and I will be recommending this stay as a beautiful place for some R & R…. Thanks for everything!!

4.96 out of 5 average rating, 25 reviews

Flat in Conway

Spacious, Sunny* Woodland Retreat

MollyRating, 5 stars3 days ago

We had a fantastic stay at Erica's with our 2 month old. Erica provided a crib, and it was safe for infant sleeping. We enjoyed sitting on the porch, and ended up cooking a full dinner for local friends one night. The kitchen had all the basics that we needed. It was a short trip so we didn't have much time to explore the property, but it looked beautiful and we enjoyed hearing the frogs at night and birds during the day. The apartment is HUGE, and we found it very comfortable. It'll be our go-to for future visits in the area!

5 out of 5 average rating, 11 reviews

Charming Family Retreat: Steps from Downtown

GabrielleRating, 5 stars1 week ago

My friends and I stayed at Jen's place for our high school reunion. The pictures did not do it justice. Not only was her place spacious, clean, and homey but it was less than a 5 minute walk to the Main Street. Jen's recommendations for coffee and food were great and the home was equipped with everything we needed, and even some things we didn't think about like books and board games. The bedrooms were all spacious and there were plenty areas for a group movie night or some quiet alone time. When we first arrived, my friends and I did not know how to lock the door. However, as soon as we reached out to Jen she responded and with patience and grace walked us through the process. My friends and I will be returning every time we visit the area ! Thank you for a great stay.

5 out of 5 average rating, 40 reviews

Guest house in Guilford

Peaceful forest cottage getaway

CourtneyRating, 5 stars4 days ago

We absolutely loved our stay!!! The trail behind the apartment is awesome, and we loved the sound of the brook. We had a turtle friend too! We hope to return!!

4.91 out of 5 average rating, 22 reviews

Flat in Greenfield

4-guest apt, easy highway access, woodsy yard

RoniRating, 5 stars2 weeks ago

Michael was most gracious and accommodating to our needs for check in and possibly needing to extend our stay. We booked Micael's place within 24 hours of arrival. He was communicating as late as midnight that he was in the space getting the place ready for us and not to worry if we needed to check in earlier. Everything would be ready. It was remarkable. We were rushing there to make it in time for our grandchild's birth and he definitely relieved our anxiety. FYI - the kitchen is very well appointed.

5 out of 5 average rating, 15 reviews

Home in Leyden

Mountaintop Views, close to private schools, golf

JasonRating, 5 stars4 days ago

Beautiful property! Fantastic deck and views, and spacious and modern inside. Great place for a weekend with friends!

4.94 out of 5 average rating, 48 reviews

Home in Guilford

Vermont Mirror House

GeorgeRating, 5 stars4 days ago

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.