
Holiday houses in Westfield
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Top-rated holiday rentals in Westfield
Guests agree: these stays are highly rated for location, cleanliness and more.

Separate apt, 1 mile from downtown, 1 guest only
This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Peaceful Snowy Lake Views from Private Hot Tub
Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Modern Comfort Meets Northampton’s Vibrant Charm
Experience the Best of Northampton! From vibrant nightlife to tranquil retreats, Northampton has something for everyone, and our newly renovated, two-bedroom duplex puts you right at the center of it all. Whether you’re catching live music, indulging in farm-to-table dining, or browsing unique local shops, every adventure is just steps away. Book your stay today and experience the perfect balance of comfort, convenience and charm in one of Northampton’s most highly rated homes!

Peaceful Meadow Retreat
Unwind at Meadow's Edge, a serene and cozy refuge where you can come to relax and recharge! Looking out on our peaceful meadow and abutting 125 acres of corn fields, this is a perfect spot to enjoy a book on the shaded back patio, a yoga or meditation session, or a quiet walk through the fields & woods. Take in the view from inside the southern facing windows, where it is not uncommon to see wildlife at dawn or dusk. This is the tranquil getaway that you have been waiting for!

Private Farm Studio Apartment
Our farm is a quiet, 5+ acre haven one mile from the center of Easthampton and 8-12 minutes from Smith College/Northampton. It's a great base from which to explore all the restaurants, cultural and outdoor activities offered in the beautiful Pioneer Valley. The private studio apartment is on the first level of our rustic farmhouse and offers a queen bed, kitchenette, living room, and bathroom. A sofabed is available for an extra $20 fee, please request this upon booking.

Studio ADU Guesthouse near Six Flags
Get ready for thrills and adventure! 🏞️🏰 Our cozy retreat is the perfect base for your Six Flags getaway! 🚗 Located just minutes away from the park, our home offers: Comfortable bedroom with plush bed Fully equipped kitchen for meal prep Relaxing living area for downtime Parking for your convenience Unwind after a day of roller coasters and excitement, and get ready to do it all again the next day! 😎 Book your stay with us and make your adventure unforgettable! 🏠👍

Farm Fresh Feeding Hills
Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Owl's Nest - Cozy Westfield Home w/ Fire Pit
Discover this simple yet sophisticated 4-bedroom, 2-bath vacation rental in the charming town of Westfield. Embrace the warmth while enjoying amenities such as a cozy fireplace and outdoor fire pit. Plus, you can savor morning coffee on the front porch or let your pup stretch its paws in the backyard. The house is also near Westfield State University and scenic hiking trails. For more to do, take a short drive to Springfield for casino thrills and local fairs!

South Quarter House
Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)

NE Historical Mansion-pets and pet lovers welcome
Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

Close AirPort|SixFlags|Big E|Free Private Parking
Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.

Linny’s Lake House - with dock
Linny’s Lake House & Dock Access 🌲🌳 Charming Lakeside Home on South Pond Welcome to our newly renovated lake house tucked into a peaceful 3/4-acre wooded lot, naturally treated to keep mosquitoes and ticks to a minimum. The setting feels calm and restorative, with gentle breezes, shaded trees, and the charm of nearby tobacco fields adding to the sense of being away without being remote.
Popular amenities for Westfield holiday rentals
Other great holiday rentals in Westfield

Large Sunny Room in Forest Park

Sunny room with private bathroom

Luxurious spacious suite in a home.

Serene getaway near Smith & Main St

Guest Room 10 Mins to Bradley Airport

Warm Country Home Minutes from Town

Simple living in Suffield

Martha's on Main
Frequently Asked Questions
Do house rentals in Westfield have wifi?
Absolutely! We offer over 10 house rentals with wifi in Westfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westfield have free parking?
Absolutely! We offer over 10 house rentals with free parking in Westfield. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Westfield?
Make yourself at home in Westfield by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Springfield Hill, over 40 vacation rentals in Hampton Ponds, and over 10 vacation rentals in Hampton Village.
How much does it cost to stay in house rentals in Westfield?
Experience the best of Westfield with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Quick stats about holiday rentals in Westfield

Total holiday rentals
Explore 10 holiday rentals in Westfield

Nightly prices starting at
Westfield holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 770 verified reviews to help you choose

Wi-Fi availability
10 of Westfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Westfield rentals

4.9 Average rating
Westfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Butternut Ski Area and Tubing Center
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- Taconic State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Norman Rockwell Museum
- Ski Sundown
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Wesleyan University
- Connecticut Science Center
- Devil's Hopyard State Park
- Clark University
- Hudson Chatham Winery
- Dcu Center




