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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Westfield and around

The Clearing - Quiet - Close To Nature
Exterior

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (195)
"Amazing views, lovely cottage!"
The Clearing - Quiet - Close To Nature
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....
East Otis Vacation Rental w/ Private Deck & BBQ!
Exterior

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (10)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Massachusetts Vacation Rental w/ Deck
Outdoor dining

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Westfield Vacation Rental w/ Porch, Pets Welcome!
Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
Historic Huntington Home - Walk to Westfield River
Exterior

Historic Huntington Home - Walk to Westfield River

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."
Historic Huntington Home - Walk to Westfield River
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Property grounds

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

10.0 out of 10, Exceptional, (6)
"Really enjoyed this cute little cottage right on the lake. Brought our 3 year old to visit family. Nice bedrooms. Gorgeous deck. Really good communication from the owner as far as directions and such. Would go back for sure. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Front of property

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
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!
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Outdoor dining

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

10.0 out of 10, Exceptional, (5)
"House was great. Great location. Clean and comfortable. No hair dryer like the listed stated. Host was quick to respond. Will stay again."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Exterior

Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard

10.0 out of 10, Exceptional, (1)
"Nice to have a Vrbo versus hotel in a quiet neighborhood. Heater wasn’t working and owner had someone there within a hour to fix it. We left our laptop and owner notified us immediately. Placed worked out great for our business trip."
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Exterior

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

10.0 out of 10, Exceptional, (44)
"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
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Outdoor dining

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

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (2 Bedrooms) | Interior

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

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Lakefront Otis Home w/ Stunning Views & Boats!
House (2 Bedrooms) | Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Exterior

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Cozy Becket Cottage Escape w/ Lake Access!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Cozy Becket Cottage Escape w/ Lake Access!
Property grounds

Cozy Becket Cottage Escape w/ Lake Access!

2.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
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 Westfield Hotel Reviews

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"Clean, courteous staff, easy access to airport and dining "
Marisol 7-night trip
Posted 5 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Frequently asked questions

Why book your cottage in Westfield with Expedia?
Expedia has some superb cottages in Westfield, so start packing for a memorable holiday close to nature. If you have a certain budget, click on how much you want to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a hot tub or a kitchen. We'll help you find the perfect pad whatever your plans or bank balance.
How can I find cheap cottages in Westfield?
The quickest way to uncover cheap cottages in Westfield is with Expedia's handy filter tool. Fine-tune your search results by star rating, budget and amenities to grab awesome rates with only a few clicks.
What is there to do in Westfield near my cottage?
The best travel accessory is a well-planned itinerary. Hampton Ponds State Park is an excellent place to begin your adventures in Westfield.