Aerial view of Greenfield, Massachusetts in winter

Greenfield Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 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$1,585 total
includes taxes & fees
28 Jun - 29 Jun
Lovely 2nd Floor Apartment
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$1,601
HK$1,998 total
includes taxes & fees
23 Jun - 24 Jun
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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$649
HK$1,801 total
includes taxes & fees
22 Jun - 23 Jun
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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$637 total
includes taxes & fees
18 Jul - 19 Jul
2 private mountain RV pads for rent. Full hook ups
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, (13 reviews)
"Yert was perfect and stocked with everything we needed,property owner showed up to make sure we had everything we needed then left us in complete privacy,location was amazing with a great scenic view."
United States
Jerry S.
The price is HK$783
HK$1,317 total
includes taxes & fees
22 Jun - 23 Jun
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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$705
HK$1,190 total
includes taxes & fees
21 Jun - 22 Jun
Yurt Oasis in the woods of Hinsdale, NH
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is HK$811
HK$1,510 total
includes taxes & fees
6 Jul - 7 Jul
Rose room Victorian home queen bed private bath
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$1,206
HK$2,325 total
includes taxes & fees
24 Jun - 25 Jun
The Studio with a View. Bring your dog, too!
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
The price is HK$846
HK$1,060 total
includes taxes & fees
18 Jun - 19 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
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$1,073
HK$3,337 total
includes taxes & fees
27 Jun - 28 Jun
Hiking Trails On-Site: Cozy Falls Brook Cabin
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (79 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$1,413 total
includes taxes & fees
22 Jun - 23 Jun
comfort, luxury, privacy
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$1,022
HK$1,483 total
includes taxes & fees
23 Jun - 24 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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$1,602 total
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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$3,213 total
includes taxes & fees
27 Jun - 28 Jun
Hiking Trails On-site: Cozy Falls Brook Cabin
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$1,026
HK$3,551 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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 HK$757
HK$1,449 total
includes taxes & fees
6 Jul - 7 Jul
2 Twin beds on 1st floor with En-suite bathroom.
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$1,860 total
includes taxes & fees
18 Jun - 19 Jun
Brookside cottage near the mountains and outdoor recreation
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$918
HK$3,452 total
includes taxes & fees
21 Jun - 22 Jun
Chalet Mount Snow/Stratton Skiing/hiking
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
18 Jun - 19 Jun
Unique and Eclectic Small Town Suite Rental in Massachusetts
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$2,154
HK$2,665 total
includes taxes & fees
18 Jun - 19 Jun
Vikings Villages Resort - Double Bed Room
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

Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

8/10 Good
"Staff was helpful in providing assistance. King sized room was okay but chair in room was poor."
Terence 5-night trip
Posted 4 hours ago
Quality Inn & Suites Northampton - Amherst

Find out more about Greenfield

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

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?

Cozy 1-bedroom house in overlooking the river close to downtown Northampton: This holiday 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?

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.