Aerial view of Greenfield, Massachusetts in winter

Greenfield Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Greenfield holiday rentals

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
The price is HK$910
HK$1,577 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$663
HK$1,835 total
includes taxes & fees
16 Jun - 17 Jun
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, (6 reviews)
"Nice place"
United States
Tom
The price is HK$1,622
HK$2,039 total
includes taxes & fees
17 Jun - 18 Jun
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
10.0 out of 10, Exceptional, (3 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is HK$698
HK$1,183 total
includes taxes & fees
14 Jun - 15 Jun
Yurt Oasis in the woods of Hinsdale, NH
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 HK$431
HK$638 total
includes taxes & fees
13 Jun - 14 Jun
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 HK$1,023
HK$1,492 total
includes taxes & fees
14 Jun - 15 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (17 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
The price is HK$1,074
HK$3,338 total
includes taxes & fees
15 Jun - 16 Jun
Hiking Trails On-Site: Cozy Falls Brook Cabin
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 HK$952
HK$1,414 total
includes taxes & fees
14 Jun - 15 Jun
comfort, luxury, privacy
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 HK$1,199
HK$3,214 total
includes taxes & fees
27 Jun - 28 Jun
Hiking Trails On-site: Cozy Falls Brook Cabin
Property grounds

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
The price is HK$846
HK$1,060 total
includes taxes & fees
13 Jun - 14 Jun
Unique and Eclectic Small Town Suite Rental in Massachusetts
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$940
HK$1,663 total
includes taxes & fees
14 Jun - 15 Jun
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, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$734
HK$3,219 total
includes taxes & fees
14 Jun - 15 Jun
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
The price is HK$1,058
HK$1,852 total
includes taxes & fees
16 Jun - 17 Jun
Brookside cottage near the mountains and outdoor recreation
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is HK$937
HK$1,668 total
includes taxes & fees
22 Jun - 23 Jun
Rose room Victorian home queen bed private bath
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is HK$666
HK$1,594 total
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"Great location. Incredible outdoor space and comfortable furnishings."
United States
Debby B.
The price is HK$1,027
HK$3,552 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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 HK$1,230
HK$2,335 total
includes taxes & fees
24 Jun - 25 Jun
The Studio with a View. Bring your dog, too!
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$2,155
HK$2,657 total
includes taxes & fees
14 Jun - 15 Jun
Vikings Villages Resort - Double Bed Room
Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is HK$1,152
HK$3,402 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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 HK$1,536
HK$4,475 total
includes taxes & fees
16 Jun - 17 Jun
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.
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Top Greenfield Hotel Reviews

Hotel Northampton

Hotel Northampton

2/10 Terrible
"The ice maker in our building didn’t work. No one mentioned that ahead of time. Also, the refrigerator wasn’t plugged in (I guess to save power). The staff was unhelpful."
Thomas Howard 1-night trip
Posted 8 hours ago
Hotel Northampton

Find out more about Greenfield

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Frequently asked questions

Are there holiday rentals in Greenfield?

Yes, there are holiday rentals close to the most popular sights 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 holiday rentals that Greenfield has to offer?

Kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley: This holiday home rental outside of Greenfield is located in the city centre, and offers a balcony, air conditioning and cable 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 Poet's Seat Tower and Old Greenfield Village.

What are holiday rentals like in Greenfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenfield. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.