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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 46 Cottages in Westfield with updated reviews, rates, and availability.

The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beach nearby, sun loungers, beach towels

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, internet, bed sheets

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Beautiful home with a great location in the Berkshires. We had a wonderful time!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Miscellaneous

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Paper towels

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
Charming Windsor Home w/ Private Backyard!
Our Cottage - Small in size, Big in character, On beautiful Highland Lake

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

10.0 out of 10, Exceptional, (43)
"Excellent place with modern decor inside and beautiful view of lake from very nice deck. Will definitely stay again! "
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Lakefront Granby Escape w/ Private Dock & Kayaks!
House (2 Bedrooms) | Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (2 Bedrooms) | 2 bedrooms, iron/ironing board, bed sheets

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Historic Huntington Home - Walk to Westfield River
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Lakefront Otis Home w/ Stunning Views & Boats!
Aerial view

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Becket Home w/ 3-season Porch: Walk to Lake Access
Interior

Becket Home w/ 3-season Porch: Walk to Lake Access

3.0 star property
Becket Home w/ 3-season Porch: Walk to Lake Access
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Lakefront Summer Cottage~Sparkling clean social distancing space

Lakefront Summer Cottage~Sparkling clean social distancing space

10.0 out of 10, Exceptional, (1)
"The hosts are lovely. The lake is clean and inviting--perfect for swimming, canoeing, kayaking, sailing, etc.. Beautiful lawn with shade and sun to relax and enjoy the view. Gorgeous flowers everywhere. Elevation helps beat the heat of the valley, keeping temps comfortable with nice breeze off lake. Fun little towns to visit. Next door to state forest with trails. Easy drive to Nothhampton. Fresh farm stand around the corner. Cottages are simple, clean and well-stocked. As hosts indicate, there...
Lakefront Summer Cottage~Sparkling clean social distancing space
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Interior

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

3.0 star property
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Springfield Vacation Rental: 1 Mi to Downtown
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Forget-me-not by Avantstay Bold Lakefront Escape
Interior

Forget-me-not by Avantstay Bold Lakefront Escape

3.0 star property
Forget-me-not by Avantstay Bold Lakefront Escape
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

3.0 star property
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
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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Other property types in Westfield

Bring Your Pet & Visit Springfield: Westfield Home
Outdoor dining

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
7.8 out of 10, Good, (6)
"The house looked like an abandoned property. It was dirty and gross. The sheets had hair on them. We actually couldn't stay. We were hopeful that after taking pictures and sending them, we have some sort of recoupment but we did not. Even though we booked through vrbo, it was apparently another company's listing and they were also no help. We won't use vrbo again. Also watch out for Evelve,"
Bring Your Pet & Visit Springfield: Westfield Home
Historic Farmhouse Near Mountains & Colleges!
Fridge, microwave, stovetop, dishwasher

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (7)
"Loved our stay at this adorable ranch home. Cute and comfy and clean. "
Historic Farmhouse Near Mountains & Colleges!
comfort, luxury, privacy
Fridge, microwave, oven, stovetop

comfort, luxury, privacy

9.8 out of 10, Exceptional, (57)
"Great place "
comfort, luxury, privacy
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.