Holiday houses in Westfield

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Top-rated holiday rentals in Westfield

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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

Apartment 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

Guesthouse 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/RV in Westhampton

4.89 out of 5 average rating, 173 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

Guest suite in Easthampton

4.96 out of 5 average rating, 448 reviews

Goreytastic Private ApARTment @ the EMC

Self-contained completely private in-law Edward Gorey inspired artistic apartment at the Easthampton Music Conservatory (right off the Williston Campus.) Romantic, campy, silly, spooky, quirky space with Edward Gorey and original artwork, a micro library including classic TV shows and popular B movies, vintage Nintendo system & oversized beanbags for Nintendo aficionados of all ages. To be clear: entirely self-contained space. Private EVERYTHING. NO shared spaces.

Top Guest favourite

Apartment 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

4.69 out of 5 average rating, 36 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 suite in East Granby

4.85 out of 5 average rating, 359 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

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Other great holiday rentals in Westfield

Superhost

Private room in Holyoke

4.85 out of 5 average rating, 110 reviews

Cosy room in historic neighborhood

StephanieRating, 5 stars3 weeks ago

Tian is very helpful. The kitchen is very big and the living room very nice to spend time in. I love staying there.

Guest favourite

Private room in Enfield

4.95 out of 5 average rating, 207 reviews

Exquisite Bedroom near I-91 with high speed Wi-Fi

JesicaRating, 5 stars3 weeks ago

Really great overnight stay at Abdul's! Clear and helpful communication around check in and the space. Comfy bed and lovely house. I've already recommended this place to a colleague.

Guest favourite

Private room in Belchertown

4.97 out of 5 average rating, 86 reviews

Sunny room with private bathroom

KevinRating, 5 stars2 days ago

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.

Top Guest favourite

Private room in Northampton

4.95 out of 5 average rating, 791 reviews

Warm Country Home Mins. from Town

AdolphRating, 5 stars3 days 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, 166 reviews

Private King Suite in Iconic Valentine Mansion

SamanthaRating, 5 stars1 week ago

I really enjoyed my stay at the Valentine Mansion. Was very unique, historical mansion. Room was comfortable. I would stay here again!

Top Guest favourite

Private room in Easthampton

5 out of 5 average rating, 83 reviews

Martha's on Main

LoriRating, 5 stars3 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

Private room in Northampton

4.98 out of 5 average rating, 237 reviews

Private luxe bedroom & bath with all the amenities

AnandaRating, 5 stars2 weeks ago

Theo’s place was the perfect clean and cozy retreat. We loved being so close to town, while also feeling a sense of peacefulness and quiet. Waking up to the beautiful garden was an added bonus! My partner and I highly recommend, and would stay again during our next visit.

Guest favourite