Greenfield Vacation Rentals

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Vacation Rentals in Greenfield

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain MA

$591 nightly

$660 total

Dec 13 - Dec 14

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.

Hot Tub

Kitchen

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.

Hot Tub

Kitchen

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.

Hot Tub

Kitchen

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont MA

$368 nightly

$411 total

Dec 13 - Dec 14

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.

Kitchen

Washer

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.

Hot Tub

Kitchen

Lovely 2nd Floor Apartment

Greenfield MA

$193 nightly

$216 total

Jan 12 - Jan 13, 2026

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.

Kitchen

Air conditioning

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.

Kitchen

Pet friendly

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.

Kitchen

Washer

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.

Kitchen

Washer

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.

Washer

Dryer

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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.