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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

4.95 out of 5 average rating, 194 reviews

Soaring 2-level loft w/ views in heart of downtown

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Guest suite in Greenfield

4.94 out of 5 average rating, 178 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.

Rental unit in Shelburne Falls

4.96 out of 5 average rating, 321 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.”

Guesthouse in Northampton

5 out of 5 average rating, 320 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Cottage in Bernardston

4.88 out of 5 average rating, 307 reviews

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 Conway

4.95 out of 5 average rating, 139 reviews

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, then known as "Goat Meadow Farm". We 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.

Guest suite in Montague

4.91 out of 5 average rating, 188 reviews

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

4.94 out of 5 average rating, 289 reviews

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.

Rental unit in Shelburne Falls

4.97 out of 5 average rating, 523 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!

Place to stay in Bernardston

4.95 out of 5 average rating, 354 reviews

Unique Private Studio w/Queen bed on second floor

Second floor studio with keyless entry and 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, 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.

Loft in Greenfield

4.97 out of 5 average rating, 98 reviews

Treehouse Retreat

This loft apartment is on the 3rd and 4th floors of a Victorian mansion. It boasts a dozen skylights and cathedral ceilings, making you feel like you're up in the trees. A jacuzzi tub, full kitchen, and large work tables make this an ideal spot for a relaxing getaway or artist's retreat. Located a couple of blocks from downtown Greenfield. Easy walk to great restaurants, cinema, shops, train station, farmers' market and co-op. 2nd bedroom with king bed and ensuite bath available for fee.

Guest suite in Charlemont

4.9 out of 5 average rating, 198 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

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Popular amenities for Greenfield vacation rentals

Free parking on premises

Air conditioning

Stay near Greenfield's top sights

Hope & Olive41 locals recommend

The People's Pint33 locals recommend

Magpie27 locals recommend

Hawks and Reed Performing Arts Center23 locals recommend

Poet's Seat Tower22 locals recommend

Green Fields Market18 locals recommend

Other great vacation rentals in Greenfield

Cabin in Cummington

4.98 out of 5 average rating, 196 reviews

Just Be Cabin

Rental unit in Plainfield

4.97 out of 5 average rating, 259 reviews

Sunny, light filled loft in 1873 Colonial

Rental unit in Pelham

4.99 out of 5 average rating, 144 reviews

Pelham 2nd floor Apartment

Home in Colrain

4.93 out of 5 average rating, 167 reviews

Secluded Farmhouse Retreat - stunning views

Rental unit in Northampton

4.94 out of 5 average rating, 327 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Cottage in Orange

4.93 out of 5 average rating, 159 reviews

The Lake Cottage: A Sweetwater Stay

Rental unit in Northampton

4.92 out of 5 average rating, 592 reviews

Sunny Peaceful Home

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 166 reviews

The Great Room in Historic Fitzwilliam

Quick stats about vacation rentals in Greenfield

Total rentals
30 properties
Total number of reviews
3.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

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 free parking, over 10 homes with a kitchen, over 10 homes with wifi, 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 10 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 apartment rentals in Greenfield have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Greenfield. Enjoy a tailored experience with all the comforts you desire.

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