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Holiday houses in Wilbraham

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Top-rated holiday rentals in Wilbraham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Apartment in Chicopee

Private 2BR Apt. Bright & Cozy, Prime Location

Fully private 2BR apt., great location & near 91 but in a quiet well-rooted neighborhood, modern and renovated, your own entrances and private porch, access to fenced yard. Sleeps up to 6. Free Internet/New Full Bath/ Full Kitchen, wash/dryer. Near MGM, Baystate, Mercy, Holyoke Hospitals, Elms College, Basketball Hall Fame, Mall, Eastern States, Jazz Fest, and Amherst. 2nd flr. Apt. In 3-family home with normal noise. Great for families, professionals, traveling nurses etc. Small pets for fee.

4.72 out of 5 average rating, 61 reviews
Guest favourite
Home in Springfield

Lemnos Experience/Game RM/MGM/BigE/SIX FLAGS

A peaceful, cozy, family-friendly retreat prioritizing safety and comfort. Our stylish space offers a luxurious yet welcoming atmosphere, ideal for relaxing and creating memories with loved ones. Conveniently located at sixteen Acres near Springfield Basketball Hall of Fame, Western New England, MGM Casino, Big E, Forest Park, Massachusetts Mutual, Six Flags, Bradley Airport, and just 45 minutes from the Berkshires and 30 minutes to UMass Amherst. Perfect for friends and families experiences!

4.95 out of 5 average rating, 20 reviews
Top Guest favourite
Guest suite in Belchertown

Serene 1-br suite on 75 acre horse property

Escape to a peaceful 1-bedroom suite on a beautiful 75-acre horse property. Tucked into the woods 1/3 mile from the main road, enjoy privacy, scenic nature trails, and views of up to 20 horses grazing in the pastures outside your windows. Relax in the guest gazebo with front-row views of the horses, perfect for morning coffee or unwinding outdoors. Enjoy a private entrance, dedicated workspace, and high-speed WiFi. Conveniently near Amherst, UMass, Smith, and Mount Holyoke Colleges.

4.98 out of 5 average rating, 174 reviews
Top Guest favourite
Tiny home in Mansfield

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

5.0 out of 5 average rating, 40 reviews
Top Guest favourite
A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.
Apartment in Northampton

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

4.97 out of 5 average rating, 498 reviews
Guest favourite
Home in Hampden

The Hampden House- a quiet country setting

Escape to serenity at our small home nestled in peaceful Hampden, outside Springfield. With its open and roomy layout, this charming property provides ample space for families to relax and unwind together. The fully fenced yard is perfect for kids and pets to run and play safely. If you're seeking a relaxing retreat or just passing through, our home has something for everyone. Book your stay and experience the serenity of country living, perfect for creating family memories.

4.89 out of 5 average rating, 70 reviews
Guest favourite
Home in West Springfield

3 Bed 2 Bath house in West Springfield.

3 bedrooms/2 baths private house located in West Springfield. 1st floor: Full Kitchen, Dining Room, Living Room, one bath with standing shower, washer&dryer; 2nd floor: 3 Bedrooms(queen size bed each) and one full bath. Parking for up to 4 cars on driveway. Self check in with keypad lock. Close to nearby restaurants, schools, shopping and other more. Easy access to Westfield, Agawam & Springfield Big E - 6min (2.3miles) Baystate - 9min(3.7miles) Six Flags-13min(6.5miles)

4.99 out of 5 average rating, 79 reviews
Top Guest favourite
Home in Chicopee

King Bed w/ Game Room near Massmutual w/ Riverview

Enjoy a stylish, spacious stay in this fully renovated home with nicely decorated bedrooms, two full baths, a full kitchen plus kitchenette, and dining for eight. Have fun in the game room with pool, arcade games, soccer board game, archery, and a huge TV. Relax on the large patio with a beautiful Connecticut River view. Perfect for families and groups seeking comfort, entertainment, and convenience. It’s also near Memorial Dr. and many local attractions and dining.

4.98 out of 5 average rating, 44 reviews
Top Guest favourite
A comfortable studio space is highlighted by a plush queen bed adorned with white bedding, positioned beside a cozy fireplace. Soft light is provided by a bedside lamp, while a fan offers air circulation. Neutral tones and warm accents create a welcoming ambiance.
Apartment in Wilbraham

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.

4.99 out of 5 average rating, 170 reviews
Guest favourite
A living area features a navy sofa paired with wooden chairs around a circular table. A stone fireplace creates a focal point, with a clock affixed above. The kitchen is visible in the background, showcasing stainless steel appliances and wooden cabinetry.
Home in Agawam

Home near Six Flags/ hot tub

Escape to our picturesque haven, perfectly situated just minutes from Six Flags thrill rides! This spacious, 11-person retreat combines rustic elegance with modern comforts, ensuring an unforgettable getaway. Unwind under starry skies in our bubbling hot tub, backyard includes patio furniture. This apartment sleeps comfortably up to 11 guests- 3 bedroom. 1st Bedroom - 2 queen beds (master suit) 2nd Bedroom - twin, queen 3rd Bedroom - bunk: twin over full, twin

4.87 out of 5 average rating, 97 reviews
Guest favourite
A serene riverside deck features two striped lounge chairs, positioned for optimal views of the Connecticut River. Lush greenery frames the scene, and flower pots add a touch of elegance. The wooden deck offers a natural and inviting space to relax by the water.
Home in Agawam

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

4.97 out of 5 average rating, 259 reviews
Guest favourite
Bungalow in Longmeadow

Elegant 3BR Longmeadow Home| Sauna| Near Big E

Welcome to your peaceful Longmeadow retreat—perfect for families visiting loved ones, Springfield events, or trips to The Big E. This charming 3BR bungalow features a wood-burning fireplace, outdoor barrel sauna, private backyard, and uplifting artistic touches. Located across from a quiet park and minutes from Springfield, the MassMutual Center, and Eastern States Exposition, it offers a relaxing place to recharge after a busy day.

4.78 out of 5 average rating, 256 reviews

Popular amenities for Wilbraham holiday rentals