Westfield Vacation Rentals

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Vacation Rentals in Westfield

Tiny Home with AC and WiFi in lovely Ludlow

Ludlow MA

$134 nightly

$150 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Ludlow, you'll be within a 15-minute drive of MassMutual Center and MGM Springfield.

Air conditioning

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.

Peace and quiet on the lake

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.

Springfield MA

Located in Springfield (South End), this vacation home is within a 15-minute walk of MGM Springfield and Naismith Memorial Basketball Hall of Fame.

Washer

Dryer

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Springfield MA

$266 nightly

$302 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Springfield (Forest Park), you'll be within a 5-minute drive of MGM Springfield and MassMutual Center.

Kitchen

Washer

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Bloomfield CT

$607 nightly

$688 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Bloomfield, you'll be within a 5-minute drive of Bloomfield Crossing and Gillette Ridge Golf Course.

Kitchen

Washer

3-bedroom house in perfect Springfield with WiFi, AC

Springfield MA

With a stay at this vacation home in Springfield (Pine Point), you'll be within a 10-minute drive of MassMutual Center and MGM Springfield.

Air conditioning

Parking available

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Becket MA

$335 nightly

$374 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Becket Quarry.

Kitchen

Pet friendly

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Windsor CT

With a stay at this vacation home in Windsor, you'll be within a 5-minute drive of Keney Park and Loomis Chaffee School.

Kitchen

Air conditioning

Newly Renovated 4 Bedroom House

Enfield CT

$421 nightly

$443 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Located in Enfield, this vacation home is within a 15-minute drive of Six Flags New England and MGM Springfield.

Kitchen

Washer

The Meadows House @ Otis Ridge w/ 7-person hot tub

Otis MA

Located in Otis, this vacation home is in the mountains, a 2-minute drive from Otis Ridge and 5 minutes from Old Baldy Wildlife Sanctuary.

Hot Tub

Kitchen

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

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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.