Vacation rentals in Greenfield

Shelburne Guest House -The Ranch

The nice thing about my home in Shelburne is the location & the peace & quiet. 10 minute drive to Greenfield Rotary I-91, easy drive to Amherst, Smith, UMass, NMH, Deerfield Academy & Stoneleigh Burnham School. Berkshire East nearby for outdoor sports. 5 minute drive to the Village of Shelburne Falls, hiking trails, bike paths, High Ledges, & the Bridge of Flowers. Updated 1964 Sears Roebuck catalog home. Bright & sunny! Large farmhouse kitchen, 3 cozy bedrooms. Large yard! Your Vacation Home!

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.

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.”

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

Peaceful Blossoms Victorian Home

This is a furnished home in Greenfield MA. It’s great for Deerfield Academy, Eaglebrook School, Northfield Mount Hermon, and Stonleigh-Burnham families. We’re close to Berkshire East, Yankee Candle, and Magic Wings. 3 bedrooms sleep up to 5, 2 baths. Circa 1890, our home has a modern kitchen, comfy couches, and an eclectic antique-heavy decor. The period layout with all bedrooms upstairs and the antique decor may not make our home ideal for people with mobility challenges or young children.

Great Falls Private Suite

Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon. We are between downtown Turners Falls and Greenfield. If you're looking for a private and bright suite with beautiful natural light and a modern bohemian feel this is the space for you! Please note that there is a kitchenette but not a full kitchen. Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the CT River.

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

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.

Modern Comfort Meets Northampton’s Vibrant Charm

Experience the Best of Northampton! From vibrant nightlife to tranquil retreats, Northampton has something for everyone, and our newly renovated, two-bedroom duplex puts you right at the center of it all. Whether you’re catching live music, indulging in farm-to-table dining, or browsing unique local shops, every adventure is just steps away. Book your stay today and experience the perfect balance of comfort, convenience and charm in one of Northampton’s most highly rated homes!

Historic Greenfield Home: Cozy Private Guest Suite

Bright comfortable guest suite just blocks from lively downtown, yet quiet, private, and easy to park. The suite has one bedroom, one living room, and one private bath; firm queen size mattress, crisp clean linens, Apple TV ready for your Netflix login, excellent high-speed wireless, private deck, and coffee bar stocked with coffee, tea, & snacks. You'll park in the rear of the house, and enjoy total privacy with your own entrance with key-code; come and go as you please.

Cozy one bedroom apartment

This is a beautiful one bedroom apartment located on the first floor that was recently remodeled. The stylish place is perfect for 2 people. It has a good size kitchen and a porch in the back. Located on a quiet and safe street yet close local restaurants and coffee shops. Easy hikes with great views like Poet Seat Tower and Highland Park. Also close to Deerfield Academy, Northfield Mount Hermon, The Bement School, Eaglebrook Schoool and Stonleigh-Burnham School.