Photo by Elizabeth Massa Peroulakis

Westfield Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Westfield

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.4 out of 10, (10)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

Westfield Vacation Rental w/ Porch, Pets Welcome!

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

Home in the Woods

10.0 out of 10, Exceptional, (1)
"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!"
The price is AU$494
includes taxes & fees
14 July - 15 July
Home in the Woods

Historic Farmhouse Near Mountains & Colleges!

3.0 star property
Historic Farmhouse Near Mountains & Colleges!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

9.6 out of 10, Exceptional, (4)
"Great property! Thank you for a wonderful stay."
The price is AU$584
includes taxes & fees
15 July - 16 July
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Charming Chicopee Getaway

The price is AU$503
includes taxes & fees
21 July - 22 July
Charming Chicopee Getaway

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (11)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (19)
"Our group had a wonderful time and we will not hesitate to book again in the future. The place was exceptionally clean, well appointed, and very comfortable. Overall it was a great experience! "
The price is AU$369
includes taxes & fees
17 July - 18 July
Easthampton Vacation Rental - Walk to Breweries!

PICON COZY

7.6 out of 10, Good, (67)
"Peaceful "
The price is AU$249
includes taxes & fees
13 July - 14 July
PICON COZY

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

9.6 out of 10, Exceptional, (31)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is AU$505
includes taxes & fees
31 July - 1 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

comfort, luxury, privacy

9.8 out of 10, Exceptional, (63)
"My wife and I were only there for one night but will definitely stay at this property again in the future, communication was quick and friendly and the apartment was clean and cozy!!!"
comfort, luxury, privacy

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (34)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is AU$552
includes taxes & fees
27 July - 28 July
Big farmhouse in the foothills of the Berkshires

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.4 out of 10, Exceptional, (13)
"This was a sweet place to stay while we were in the area for a graduation. It is a beautiful little apartment with everything we needed, cozy and quiet, and Lucienne’s communications were clear and welcoming!"
The price is AU$323
includes taxes & fees
15 July - 16 July
Newly Built Barn Loft in Pioneer Valley

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

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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

10.0 out of 10, Exceptional, (1)
"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."
The price is AU$815
includes taxes & fees
14 July - 15 July
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (7)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .

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

9.4 out of 10, Exceptional, (21)
"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is AU$257
includes taxes & fees
13 July - 14 July
HOMEY HOMEY

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (7)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find a holiday rental in Westfield?

Yes, there are holiday rentals in Westfield close to Whitney Park, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Westfield has to offer?

Bring Your Pet & Visit Springfield: Westfield Home: This highly rated holiday home rental in Westfield offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Westfield?

With 4 Expedia holiday rentals, you're guaranteed 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 Chapman Park are a couple of great spots to enjoy the outdoors. While here, Hampton Ponds State Park and Robinson State Park are other places worth a visit.

What are holiday rentals like in Westfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westfield. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family getaway.