Vacation rentals in Wilbraham

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Top-rated vacation rentals in Wilbraham

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

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Top guest favorite
Cottage in Brimfield
4.98 out of 5 average rating, 106 reviews

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

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Top guest favorite
A decorative sign reading 'Little House Inn' is visible beneath a flowering tree. Circular images feature a cozy living area with multiple windows, scenic views of seasonal foliage, and tranquil outdoor spaces, highlighting the surrounding nature and inviting atmosphere.
Home in Ware
4.9 out of 5 average rating, 352 reviews

Little House Inn - Private House - Secluded

Reconnect with loved ones in our peaceful and cozy, family-friendly home. Our little house is situated on an acre & a half of land surrounded by wetlands and woods yet minutes from local colleges and amenities. Enjoy the beautiful night sky while relaxing by the fire pit. Or take in the woodland view from your deck with your morning coffee and yoga workout (mat provided). Deer, turkeys, bunnies, & many native birds are regular visitors. Check out our guidebook for places to eat & things to do.

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Guest favorite
Apartment in Chicopee
4.73 out of 5 average rating, 60 reviews

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.

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Top guest favorite
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
4.97 out of 5 average rating, 494 reviews

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.

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Guest favorite
Home in Stafford
4.94 out of 5 average rating, 110 reviews

Serene Lakefront Retreat

This idyllic 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake accommodates up to 6 guests (4 beds), offering an unforgettable experience for your family. Enjoy breathtaking views from the cozy living area or the private deck. Kayak (2 included), swim off the floating dock, stargaze, grill out and enjoy your coffee on the deck! Separate workspace and free Wi-Fi for those working from home. Perfect for Brimfield Antique attendees. Book now for a relaxing getaway!

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Guest favorite
Home in Hampden
4.88 out of 5 average rating, 69 reviews

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.

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Top guest favorite
A well-maintained home is situated on a gentle slope, featuring a neatly landscaped front yard with flowering plants and shrubs. An American flag is displayed by the entrance, and a gravel driveway leads to the garage below, surrounded by lush greenery.
Home in Amherst
5.0 out of 5 average rating, 184 reviews

The Suprenant House

Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.

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Guest favorite
Home in West Springfield
4.99 out of 5 average rating, 77 reviews

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)

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Top guest favorite
Home in Chicopee
4.98 out of 5 average rating, 44 reviews

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.

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Top guest favorite
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
4.99 out of 5 average rating, 170 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.

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Guest favorite
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
4.97 out of 5 average rating, 259 reviews

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.

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Guest favorite
Bungalow in Longmeadow
4.78 out of 5 average rating, 255 reviews

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.

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Popular amenities for Wilbraham vacation rentals