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Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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Rental unit in Shelburne Falls

In town, newly renovated studio with private deck

Come explore our unique area and stay in a newly 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!

Rental unit in Greenfield

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 newly renovated 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, key-code entry door; come and go as you please.

Cottage in Bernardston

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.

Rental unit in Shelburne Falls

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.”

Rental unit in Greenfield

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen 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.

Guest suite in Greenfield

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. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to the Canadian border.

Guest suite in Montague

Great Falls Private Suite

Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the Connecticut River. Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon, 2 miles from downtown Turners Falls and 2.6 miles from downtown Greenfield. If you are looking for a private and bright suite with beautiful natural light and a modern bohemian feel this guest retreat is for you. I look forward to hosting you!

Loft in Shelburne Falls

The Railroad House

The Railroad House is a cute attached converted barn in the village center with parking, private entrance, 2 floors, fridge, microwave, coffee maker, toaster, WiFI, but no television. It is located within just a minute's walk from the famous Bridge of Flowers. Other local attractions include several dining choices from a drugstore soda shop on up to 5-star dining, as well as the country's 2nd oldest bowling alley. On weekends you can often find live music. Train goes by twice/day on average.

Guest suite in Sunderland

Bright private suite mins. from Five College area

Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Café. Suite is professionally cleaned between each stay.

Home in Williamsburg

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.

Place to stay in Bernardston

Stylish Private Studio w/Queen bed and Coded Locks

Second floor studio with large eat in kitchen in quiet, rural, residential area. Outdoor yard space for guest use. 15 min. walk to country store, bakery, 2 pizza shops, brewery, gas station with Dunkins, library, and Post Office. Easy access to Rt 91 and Rt 2. Eight min drive to Greenfield, 15 to Brattleboro, 20 to Northampton. Close to Northfield Mt Hermon, Stoneleigh Burnham, Deerfield Academy and Thomas Aquinas College. Close to VT and NH and 30-90 minutes to many ski slopes.

Cottage in Ashfield

hope house

Sunny and open writing studio with over 150 years of literary history. Built in 1870, this lovely little house was where George Curtis edited Harper's magazine, wrote essays on transcendentalism , and argued for women's suffrage ( A recent guest informs me that George Curtis helped Thoreau build his cabin on Walden Pond ) The house has since sheltered painters, librarians, and poets.

Vacation rentals for every style

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Popular amenities for Greenfield vacation rentals

Free parking on premises

Air conditioning

Stay near Greenfield's top sights

Poet's Seat Tower22 locals recommend

Green River Swimming and Recreation Area6 locals recommend

Terrazza Restaurant at CCG9 locals recommend

Other great vacation rentals in Greenfield

Rental unit in Plainfield

Sunny, light filled loft in 1873 Colonial

Cottage in Orange

The Lake Cottage: A Sweetwater Stay

Guesthouse in Northampton

Mill River Cottage (pet friendly!)

Rental unit in Winchester

Downtown Loft above Winery and Distillery

Guest suite in Brattleboro

Charming studio in renovated 19th century church.

Rental unit in Shelburne Falls

Big, sunny 1893 flat steps from Bridge of Flowers

Guest suite in Charlemont

Unique People & Pet-Welcoming Haven

Rental unit in Northampton

Sunny Peaceful Home

Quick stats about vacation rentals in Greenfield

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2.8K reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Greenfield?
Four-legged friends are welcome in Greenfield. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Greenfield?
Greenfield has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Greenfield?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in apartment rentals in Greenfield?
Experience the best of Greenfield with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Greenfield?
Yes! Work meets play with ease at over 20 vacation rentals in Greenfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Greenfield have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greenfield have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenfield have wifi?
Absolutely! We offer over 10 house rentals with wifi in Greenfield. Enjoy a tailored experience with all the comforts you desire.

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