A snow-covered town with a prominent church steeple, red brick buildings, and a clear blue sky.

Greenfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Greenfield vacation rentals

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful, thoughtful space on a gorgeous piece of property. "
United States
Jodi W.
The price is ￥18,771
￥32,708 total
includes taxes & fees
Jul 14 - Jul 15
Lovely 2nd Floor Apartment
Exterior detail

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (8 reviews)
"We had a great"
United States
Meredith B.
The price is ￥20,226
￥46,252 total
includes taxes & fees
Jul 12 - Jul 13
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (8 reviews)
"Nice place"
United States
Tom
The price is ￥32,740
￥41,628 total
includes taxes & fees
Jul 13 - Jul 14
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (14 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is ￥18,771
￥30,014 total
includes taxes & fees
Jul 13 - Jul 14
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,892
￥13,157 total
includes taxes & fees
Jul 12 - Jul 13
2 private mountain RV pads for rent. Full hook ups
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is ￥21,099
￥30,792 total
includes taxes & fees
Jul 13 - Jul 14
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (81 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is ￥19,644
￥29,167 total
includes taxes & fees
Jul 12 - Jul 13
comfort, luxury, privacy
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (1 review)
"Staff was super friendly, host was also amazing!"
United States
Connor
The price is ￥17,623
￥22,045 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Exterior

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is ￥15,432
￥29,699 total
includes taxes & fees
Jul 13 - Jul 14
2 Twin beds on 1st floor with En-suite bathroom.
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥19,483
￥34,638 total
includes taxes & fees
Jul 13 - Jul 14
Private bed with En-suite bathroom Marigold Room
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (12 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥16,498
￥68,294 total
includes taxes & fees
Jul 13 - Jul 14
Chalet Mount Snow/Stratton Skiing/hiking
Iron/ironing board, WiFi, bed sheets

Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is ￥27,162
￥59,779 total
includes taxes & fees
Aug 11 - Aug 12
Cozy private 2 bed apartment in Shelburne Falls
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is ￥27,162
￥51,246 total
includes taxes & fees
Jul 22 - Jul 23
The Studio with a View. Bring your dog, too!
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
The price is ￥29,387
￥66,671 total
includes taxes & fees
Aug 5 - Aug 6
Hiking Trails On-site: Cozy Falls Brook Cabin
Interior

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ￥39,463
￥81,102 total
includes taxes & fees
Jul 14 - Jul 15
Button's Modern Luxury Walkup Downtown Northampton
Dining

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is ￥36,055
￥98,176 total
includes taxes & fees
Jul 22 - Jul 23
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Exterior

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is ￥33,953
￥84,746 total
includes taxes & fees
Jul 13 - Jul 14
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥44,462
￥55,180 total
includes taxes & fees
Jul 12 - Jul 13
Vikings Villages Resort - Double Bed Room
Terrace/patio

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (3 reviews)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is ￥44,624
￥87,409 total
includes taxes & fees
Jul 28 - Jul 29
Terrific 3-bedroom unit in charming Leverett with AC
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is ￥29,038
￥76,166 total
includes taxes & fees
Jul 22 - Jul 23
Stunning Glass House nestled in the Vermont wilderness!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenfield Hotel Reviews

Hotel UMass

Hotel UMass

10/10 Excellent
"So convenient to stay on campus? Room was comfortable with a great view."
Lisa 2-night trip
Posted 10 hours ago
Hotel UMass

Find out more about Greenfield

Search for holiday rentals in Greenfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenfield using one of the methods below:

  • View our selection of featured holiday rentals in Greenfield
  • Use the map to find apartments and other holiday homes in the Greenfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenfield while they last

Look no further and take a look at our great range of rental properties in Greenfield!

Frequently asked questions

Are there vacation rentals in Greenfield?

Yes, we have vacation rentals close to the most popular attractions in Greenfield, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Greenfield is known for its shops. Make sure you have time to check out the breweries and live music during your trip.

What are some of the best vacation home rentals that Greenfield has to offer?

Cozy 1-bedroom house in overlooking the river close to downtown Northampton: This vacation home rental outside of Greenfield has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What can I see and do in Greenfield?

Connecticut River and Energy Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Old Greenfield Village and Poet's Seat Tower.

What are vacation rentals like in Greenfield?

Vacation rentals are privately owned properties you can book for several days or longer in Greenfield. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.