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
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Greenfield vacation rentals

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is ￥18,430
￥31,936 total
includes taxes & fees
May 20 - May 21
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)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is ￥19,573
￥44,205 total
includes taxes & fees
May 20 - May 21
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
9.6 out of 10, Exceptional, (4 reviews)
"We had a lovely stay at this spot. We came in for the weekend for a family wedding and it was the perfect central location to bounce around out of for the ceremony & visiting everyone. The house is also super cool!"
United States
Victoria S.
The price is ￥19,430
￥25,249 total
includes taxes & fees
May 19 - May 20
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, (12 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.
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
House (4 Bedrooms) | Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is ￥24,287
￥82,787 total
includes taxes & fees
May 19 - May 20
Outdoor Adventure Hub! Family Home in West Dover
2 bedrooms, desk, iron/ironing board, travel crib

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 ￥20,716
￥30,232 total
includes taxes & fees
May 21 - May 22
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, (78 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 ￥19,287
￥28,637 total
includes taxes & fees
May 19 - May 20
comfort, luxury, privacy
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥26,986
￥47,648 total
includes taxes & fees
May 25 - May 26
Wellness Getaway with a Personal Sauna, and Private River Beach!
4 bedrooms, travel crib, internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"The house was just as listed. Everything we needed was there for us upon arrival. The host is amazing and was happy to welcome us in their home. We would definitely come back"
United States
Louis
The price is ￥21,747
￥86,302 total
includes taxes & fees
May 19 - May 20
Outdoor Adventure Hub! Family Home in West Dover
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 ￥22,224
￥44,092 total
includes taxes & fees
May 26 - May 27
The Studio with a View. Bring your dog, too!
Outdoor dining

Historic downtown apartment. Unscented products and sustainability practices.

Historic downtown apartment. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (11 reviews)
"Quite a find in pricey Northampton. Within easy walking distance to restaurants and shops. Small but very comfortable. We didn't spend much time in the apartment, but it was perfect for what we needed."
United States
Jessica B.
The price is ￥29,208
￥53,725 total
includes taxes & fees
May 19 - May 20
Historic downtown apartment. Unscented products and sustainability practices.
Property grounds

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is ￥31,748
￥96,115 total
includes taxes & fees
May 19 - May 20
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is ￥25,716
￥48,229 total
includes taxes & fees
May 19 - May 20
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥31,589
￥38,778 total
includes taxes & fees
May 19 - May 20
Vikings Villages Resort - Double Bed Room
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (1 review)
"This place is simply fantastic. If you are looking for quiet...and I mean ABSOLUTE quiet...this is your place! Nestled just five minutes south of Readsboro, VT, Brookside Cottage is the place to get disconnected and just breathe a bit. Our family needed this place...I needed to be here...with our kids growing up so fast, now at 14 and 11, my wife and I just wanted to have a few days to be together, play some games, watch some movies, and enjoy each other's company. I'm convinced we found the...
United States
Jason H.
The price is ￥21,430
￥37,691 total
includes taxes & fees
May 20 - May 21
Brookside cottage near the mountains and outdoor recreation
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"Everything great!"
United States
Andrew P.
The price is ￥63,496
￥95,573 total
includes taxes & fees
May 24 - May 25
Bear Creek Cabin
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 ￥23,144
￥67,879 total
includes taxes & fees
May 20 - May 21
Stunning Glass House nestled in the Vermont wilderness!
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 ￥31,589
￥80,360 total
includes taxes & fees
May 19 - May 20
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Fridge, microwave, oven, stovetop

Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (7 reviews)
"The house was very comfortable and we enjoyed our visit very much "
United States
Debbie L.
The price is ￥58,416
￥107,273 total
includes taxes & fees
May 31 - Jun 1
Historic downtown house. Unscented products and sustainability practices.
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, (18 reviews)
"Great place!"
United States
Jack & Heather G.
The price is ￥31,113
￥90,829 total
includes taxes & fees
May 26 - May 27
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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

2/10 Terrible
"We found 3 bugs in our room- they weren’t bed bugs maybe some type of stink bug the very kind manager suggested. For the price we had to pay for grad weekend we shouldn’t have been forced to deal with dead bugs. The hotel is old, out dated and had a musty smell. The manager was so nice but that is about all I can say."
Deborah 2-night trip
Posted 3 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?

Kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley: This vacation home rental outside of Greenfield is located in the city center and offers a balcony, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Greenfield?

Energy Park and Connecticut River 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.