Apartment holiday rentals in Western Massachusetts

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Northampton MA Downtown Townhouse close to Smith

Discover the charm of Northampton from our unique Townhouse apartment nestled in a National Register of Historic neighborhood. This is more than just a place to stay. it's an invitation to experience the rich tapestry of vibrant community. 3 minutes walk to downtown Northampton, where you will enjoy from an array of shops, local restaurants, art galleries, cafes, music venues & the Amtrak station. Whether you're here for business or pleasure, you're at the epicenter of culture & convenience.

Steps to MoCA: 2bd + SAUNA!

Near ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and others. A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

Forest Hideaway—Light, Privacy, Washer/Dryer

Wake up among 100-year-old trees, then drive ten minutes into Amherst. Or hike out the door toward wooded trails. The apartment sits with our house on 5 acres of mature forest, high on a hill and facing the woods. With a kitchen & washer/dryer, the apartment is peaceful and practical, ideal for a weekend getaway or an extended stay, great for academics needing space for contemplation or for a couple visiting family. (Read about the steep driveway if planning a winter trip.)

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly a dog, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

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.

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.