Westfield Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Westfield

Private kitchen
Home in the Woods

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
$303 nightly
The price is $320
Dec 5 - Dec 6
Total with taxes and fees
Home in the Woods
Fridge, microwave, oven, stovetop
Owl`s Nest - Cozy Westfield Home w/ Fire Pit

Owl`s Nest - Cozy Westfield Home w/ Fire Pit

Westfield
9.6 out of 10, Exceptional, (7)
"Great place for a large family get together, convenient to downtown Westfield. Nice big fenced yard, good for dogs. "
United States
Harry M.
Owl`s Nest - Cozy Westfield Home w/ Fire Pit
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow

Ludlow
8.4 out of 10, Very Good, (8)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
$134 nightly
The price is $150
Dec 5 - Dec 6
Total with taxes and fees
Tiny Home with AC and WiFi in lovely Ludlow
Dining
The Serene Skyway Retreat

The Serene Skyway Retreat

Windsor Locks
8.8 out of 10, Excellent, (11)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
$256 nightly
The price is $272
Dec 8 - Dec 9
Total with taxes and fees
The Serene Skyway Retreat
Terrace/patio
Peaceful Meadow Retreat

Peaceful Meadow Retreat

2.0 star property
Granby
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
$176 nightly
The price is $200
Dec 7 - Dec 8
Total with taxes and fees
Peaceful Meadow Retreat
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Boston Road
9.2 out of 10, Wonderful, (13)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
$283 nightly
The price is $321
Dec 7 - Dec 8
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms

Holyoke
9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
$288 nightly
The price is $322
Dec 7 - Dec 8
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Dining
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Boston Road
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
$283 nightly
The price is $321
Dec 5 - Dec 6
Total with taxes and fees
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Property grounds
Welcome to Honey Spot!

Welcome to Honey Spot!

Pine Point
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
$262 nightly
The price is $297
Dec 31 - Jan 1, 2026
Total with taxes and fees
Welcome to Honey Spot!
Smart TV
PICON COZY

PICON COZY

Sixteen Acres
7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
United States
Linda W.
$151 nightly
The price is $171
Dec 26 - Dec 27
Total with taxes and fees
PICON COZY
Microwave, oven, stovetop
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Enfield
10.0 out of 10, Exceptional, (2)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
$372 nightly
The price is $421
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Fridge, microwave, oven, stovetop
Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed

Chicopee
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
$339 nightly
The price is $385
Dec 7 - Dec 8
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Fridge, microwave, oven, stovetop
Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway

Forest Park
8.8 out of 10, Excellent, (3)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
$301 nightly
The price is $341
Dec 7 - Dec 8
Total with taxes and fees
Newly Beautiful renovated first floor apartment getaway
Fridge, microwave, oven, stovetop
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks
10.0 out of 10, Exceptional, (2)
"We loved this space for our short stay. The rooms and space were cozy with a fun theme. Everything was clean and check in/out was easy. The host was responsive and helpful. We would stay here again"
United States
Amanda W.
$393 nightly
The price is $445
Dec 7 - Dec 8
Total with taxes and fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Smart TV, books, stereo
Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley

2.0 star property
Belchertown
9.4 out of 10, Exceptional, (22)
"cute little place! host was very responsive"
United States
zane s.
$201 nightly
The price is $212
Dec 14 - Dec 15
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Charming Chicopee Getaway

Chicopee
7.4 out of 10, Good, (3)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
$267 nightly
The price is $311
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Granby
9.4 out of 10, Exceptional, (20)
"Great overnight stay! "
United States
Carrie M.
$255 nightly
The price is $269
Dec 5 - Dec 6
Total with taxes and fees
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
3 bedrooms, iron/ironing board, WiFi, bed sheets
Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home

2.0 star property
Chicopee
$298 nightly
The price is $338
Dec 8 - Dec 9
Total with taxes and fees
Welcoming 3-bedroom house- Gardner home
Property grounds
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

East Granby
8.6 out of 10, Excellent, (4)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
$387 nightly
The price is $439
Dec 9 - Dec 10
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Property grounds
The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
$248 nightly
The price is $277
Dec 8 - Dec 9
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Everything was perfect no issues at all"
Michael 1-night trip
Posted 11 hours ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Westfield

Everything you need to know about Westfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Westfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westfield rentals

At Expedia, we put the best Westfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Westfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Westfield?

Yes, we offer vacation rentals in Westfield near Whitney Park, or you can choose a secluded option if you'd like a relaxing place to stay. Our travelers say Westfield has a good selection of restaurants. Make sure you have time to check out the shopping while you're in the area.

What are some of the best vacation rentals that Westfield has to offer?

Peace and quiet on the lake: Visitors like this Westfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Westfield?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Westfield stay.

What can I see and do in Westfield?

Family-friendly attractions include Whitney Park and Cross Street Playground, whereas Westfield River and Wojtkiewicz Park are a couple of great spots to enjoy the outdoors. While here, Westfield Athenaeum and Hampton Ponds State Park are other places worth a visit.

What are vacation rentals like in Westfield?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Westfield. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.