Greenfield Vacation Rentals

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Vacation Rentals in Greenfield

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain MA

$687 nightly

$768 total

Dec 28 - Dec 29

Total with taxes and fees

Located in Colrain, this vacation home is within a 5-minute drive of Arthur A. Smith Covered Bridge and Colrain Town Hall.

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington VT

Located in Wilmington, this vacation home is on the waterfront, within a 5-minute walk of Deerfield River and Harriman Reservoir.

Experience Three Sisters Sanctuary in Goshen, MA

Goshen MA

Located in Goshen, this vacation home is a 1-minute drive from Three Sisters Sanctuary and 7 minutes from Steady Lane/Hill Cemetery.

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT

Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont MA

$368 nightly

$411 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Charlemont, you'll be a 4-minute walk from Charlemont Federated Church and 5 minutes by foot from Charlemont Historical Society and Museum.

Washer

Dryer

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Shelburne Falls MA

With a stay at this vacation home in Shelburne Falls, you'll be a 1-minute walk from Deerfield River and 7 minutes by foot from Arms Cemetery.

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Whitingham VT

Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.

Lovely 2nd Floor Apartment

Greenfield MA

$180 nightly

$201 total

Dec 14 - Dec 15

Total with taxes and fees

Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Northampton MA

With a stay at this vacation home in Northampton, you'll be within a 15-minute drive of University of Massachusetts Amherst and Don Muller Gallery.

StrautmanHaus - All-Season Chalet at Berkshire East

Charlemont MA

With a stay at this vacation home in Charlemont, you'll be within a 5-minute walk of Berkshire East Ski Resort and Thunderbolt Mountain Coaster.

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Amherst MA

$1,538 nightly

$1,718 total

Jan 9 - Jan 10, 2026

Total with taxes and fees

With a stay at this vacation home in Amherst, you'll be a 2-minute walk from University of Massachusetts Amherst and 6 minutes by foot from Brown Fine Arts Center.

Cabin Style Rustic Getaway, with mini-splits

Northampton MA

With a stay at this vacation home in Florence, you'll be within a 5-minute drive of Look Memorial Park and Congregation Beth Israel.

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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.