Holiday rentals in Westfield

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Top-rated holiday rentals in Westfield

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Guest favourite

Townhouse in Chicopee

4.98 out of 5 average rating, 40 reviews

King Bed w/ Pool Table – Cozy Stay Near MassMutual

Welcome to our charming townhome, a perfect getaway for families, couples, or solo travelers. Whether you're here for a relaxing retreat or an action-packed adventure, this home has the amenities to make you feel at home. The thoughtfully designed space balances relaxation and entertainment, making it the ideal base for your trip. It’s near Memorial dr. & many local attractions and dining. Want a tour? Search "The Buckley Home Chicopee/Springfield MA Airbnb 3 bedroom 1.5 walkthrough" on YouTube

Top guest favourite

Place to stay in West Springfield

4.95 out of 5 average rating, 41 reviews

Entire studio with deck

Welcome to my cozy, independent entrance studio/in-law mini apartment, located in West Springfield, MA. Maritza’s studio is perfect for a single person or a couple who wants to experience the beauty of a nice, safe, peaceful neighborhood. No suitable for infants. The studio is conveniently located near Big E, Six Flags, Basketball Hall of Fame, museums, nice restaurants,the MGM Casino, Yankee candle. 15 minutes from Baystate and Mercy Hospitals in Springfield and Noble Hospital in Westfield.

Top guest favourite

Cottage in Southwick

4.98 out of 5 average rating, 110 reviews

4 Kayaks Fire Pit & Lake Views from 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 2 families. (4 adults w/4 kids or 6 adults) 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

Guest favourite

Flat in Westfield

4.92 out of 5 average rating, 49 reviews

Cozy Apartment

Surround yourself with style in this standout space. You will feel like you are at home. Enjoy a peaceful escape in this beautifully equipped rental in the center of Westfield, just minutes from downtown! This lovely remodeled unit offers new vinyl floors, new kitchen, all furnished for you, spacious bedroom with lots of natural light. It has 2 stair flights, Its perfect location for easy access to many popular attractions within the city limits as well as Big E which is only 15 min away.

Guest favourite

Guest suite in Easthampton

4.92 out of 5 average rating, 265 reviews

The Floating Library: private hiker's hideaway

Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming, above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and lots of magical touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

Top guest favourite

Guest house in Granby

4.97 out of 5 average rating, 38 reviews

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!

Guest favourite

Campervan/Motorhome in Westhampton

4.89 out of 5 average rating, 172 reviews

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Top guest favourite

Flat in Wilbraham

4.98 out of 5 average rating, 111 reviews

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Guest favourite

Home in Feeding Hills

4.89 out of 5 average rating, 977 reviews

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.

Top guest favourite

Home in Russell

4.96 out of 5 average rating, 265 reviews

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.)

Superhost

Tiny home in Montgomery

4.74 out of 5 average rating, 35 reviews

Tiny house at Misty's Meadow! (Turtle Bend Farm)

⚠️ TWIN BED! Relax in a picturesque valley on a 30 acre permaculture farm, in an off-grid tiny house. Nice windows for summer breezes. Organic cotton bedding. 🍑 With sweeping views of a sunny pasture, enjoy the antics of cows, calves, sheep and donkeys as they graze. 🐄 Numerous local trails and swim spots abound - Shatterack Mountain trailhead. 🌿 Lvl 2 EV charging available Note: Trains go through the valley every so often.

Guest favourite

Guest house in Enfield

4.94 out of 5 average rating, 35 reviews

Close BDL AirPort & SixFlags 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.

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Other great holiday rentals in Westfield

Guest favourite

Private room in Belchertown

4.97 out of 5 average rating, 86 reviews

Sunny room with private bathroom

KevinRating, 5 starstoday

The room looked just like the photos and m matched the description perfectly. It was clean and tidy, and the bathroom was spotless. The neighborhood is quiet and private. Yulia was very friendly and helpful throughout my visit. Overall, it’s a great value for the price, and I would definitely recommend staying here.

Guest favourite

Private room in Agawam

4.92 out of 5 average rating, 185 reviews

Super nice Agawam retreat 2

NoreenRating, 5 stars3 weeks ago

Timothy was a great host with excellent communication skills. It was easy to find and very convenient to the highway. The neighborhood was very quiet while being close to amenities. I always fully appreciate staying where my dogs are welcome too.

Top guest favourite

Private room in Northampton

4.95 out of 5 average rating, 791 reviews

Warm Country Home Mins. from Town

AdolphRating, 5 stars1 day ago

Super friendly and responsive hosts, but also very accommodating when I wanted privacy. Very comfortable bed, very clean room and bathroom, little amenities in the bathroom provided free of charge. Fresh coffee available every morning. Had access to my own fridge in the kitchen. The home is a seven minute drive from the middle of Northampton, set in a semi rural and very quiet area. Serves as a nearby location to all the town’s attractions, but offers real escape from it all when you want it. This is my second time staying with Rachel and David, and I hope to do it again soon.

Superhost

Private room in South End

4.78 out of 5 average rating, 165 reviews

Private King Suite in Iconic Valentine Mansion

AlainaRating, 5 stars1 month ago

It was such a treat to rest and relax in this beautiful historic mansion. The Maple room was the perfect getaway for a mini-vacation between legs of a road trip to see my nephews. The bedroom, private bathroom, and balcony were spotlessly clean and peaceful spaces in which to rejuvenate. Originally, I was going to leave quite early in the morning, but after arriving at 10:30pm after work, I decided to take me time in the morning and enjoy tea in the silver sunroom and marvel at the hand-carved fireplace and sit outside on the balcony. What a special place. It would be fun to stay longer next time and visit Springfield. (I have explored it before and there are good restaurants and fun things to do.) Thank you, Katherine, for sharing the joy and wonder this space brings.

Top guest favourite

Private room in Easthampton

5 out of 5 average rating, 83 reviews

Martha's on Main

LoriRating, 5 stars2 weeks ago

We had a great time at Martha's. The home was very clean and Martha was very hospitable. She is very friendly and went out of her way to help us feel at home. As advertised the bathroom is not attached to the bedroom, but it is exclusively for use by the Airbnb guest.

Top guest favourite