Holiday houses in South Hadley

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Top-rated holiday rentals in South Hadley

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

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Top Guest favourite
A cozy living area is presented, featuring a contemporary gray sofa and a yellow accent chair. A minimalist coffee table is centered on a colorful patterned rug. A black fireplace with a mirror above it adds a focal point, while natural light fills the space through nearby windows.
Guest suite in Northampton
4.93 out of 5 average rating, 125 reviews

Bright Noho studio suite perfect walk to downtown

Stay in the heart of Northampton in this charming studio with a private deck—perfect for unwinding after a day of exploring. A short walk to downtown, Smith College, museums, shops, and top restaurants, this location puts the best of the Pioneer Valley at your doorstep. Whether you're here for Parents' Weekend, a getaway, a show at the Iron Horse, or to explore the area's beauty, you'll love the comfort & convenience of this space. Easy commute to Smith, Amherst, UMass, and Hampshire College.

Top Guest favourite
A rustic barn structure sits on a vast green lawn, framed by rolling hills in the background. The barn features a metal roof and wooden siding, with a small red building visible nearby. Fluffy white clouds drift across a bright blue sky.
Cottage in Hadley
4.96 out of 5 average rating, 57 reviews

Loft with Sweeping Views

Nestled on a farm in Hadley, MA, the 384-square-foot Loft is perched above a woodworking shop, offering sweeping views of Skinner Mountain and tranquil farmland. With a queen bed, day bed, kitchenette, full bath, the Loft has served as a spot for college visits, sibling reunions, a writer's retreat, and a wedding suite. It's quiet and distraction-free, yet close to local dining, gyms, and amenities. Reserve this magical spot today! Note: Parties are not allowed, neither indoors nor outdoors.

Top Guest favourite
A functional kitchen features wooden cabinetry and a dining table surrounded by chairs, providing a space for shared meals. Appliances include an oven, microwave, and full-sized refrigerator. Natural light enhances the warm ambiance, while the door leads to the outside.
Guest suite in Easthampton
4.93 out of 5 average rating, 307 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
An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.
Cabin in Williamsburg
4.97 out of 5 average rating, 121 reviews

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Top Guest favourite
A charming blue cottage is depicted, featuring a welcoming yellow front door and large windows. A stone pathway leads to the entrance, surrounded by natural landscaping. Tall pine trees offer shade, while a white picket fence encloses the property.
Home in South Hadley
5 out of 5 average rating, 65 reviews

Charming Riverfront Cottage

Charming 2 bedroom, 1 bathroom cottage on a peaceful cove of the Connecticut River. Enjoy bird life, water views and magical sunsets in this nature lovers’ paradise. Bright and airy throughout. Fully equipped kitchen. Two bedrooms on the first floor, with a loft space upstairs with a futon couch/bed. Two TV's (Roku). We've provided 2 touring kayaks (longer/heavier than other kayaks) in the shed. We recommend at least one strong person and bring water shoes (the bottom is yucky)!

Top Guest favourite
Home in Chicopee
5 out of 5 average rating, 29 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.

Guest favourite
The exterior of a charming house is framed by vibrant autumn foliage, including trees with bright yellow and red leaves. A stone chimney adds character to the roof, while a wooden fence borders the well-maintained garden. Soft light highlights the warm colors of the scene.
Apartment in Amherst
4.9 out of 5 average rating, 294 reviews

Amherst, Quiet, Private, Cozy Studio Apartment

This cozy studio is ideally located for exploring nearby colleges: UMass, Hampshire, Amherst, Mount Holyoke, and Smith. Nestled in the scenic Pioneer Valley, enjoy stunning landscapes, forests, and rivers, as well as cultural highlights like the Eric Carle Museum, Yiddish Book Center, and Emily Dickinson Museum. Just minutes from hiking trails, art galleries, gourmet dining, and music venues, our studio offers the perfect base for your Pioneer Valley adventure.

Top Guest favourite
A living room is displayed, featuring a comfortable blue couch adorned with patterned pillows. Three framed landscape images are mounted on the wall above a wooden coffee table. Natural light enters through a window with sheer curtains, illuminating a cozy reading nook in the background.
Apartment in Northampton
4.99 out of 5 average rating, 253 reviews

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

Guest favourite
Guest suite in Holyoke
4.84 out of 5 average rating, 271 reviews

Lovely 1 Bedroom w private entrance

Ground floor apartment with private entrance and parking on a quiet circle road. The apartment includes a "mini kitchen" with microwave, small fridge with freezer, and some kitchen basics. The unit also includes a washer and dryer! Recently renovated private bathroom. Very centrally located, 15 mins from Downtown Northampton and Springfield, 20 minutes to Amherst, central to all area colleges, and 1 hour from the beauty of the Berkshires! All are welcome!

Guest favourite
The exterior of the guest suite showcases a brown shingle facade, featuring a welcoming front porch with white railing. A concrete pathway leads to the entrance, while a grassy area and trees provide a natural backdrop. The driveway offers ample parking space.
Guest suite in South Hadley
4.93 out of 5 average rating, 169 reviews

Peaceful 1BR | Private Two-Story Retreat Near MHC

Enjoy this private, two-story 1-bedroom, 1-bath suite in a beautifully renovated vintage house! With a full kitchen, cozy living room, and upstairs bedroom and bath, it’s perfect for individuals, couples or small families. Relax inside in a peaceful space, walk to Mount Holyoke College and Village Commons, or explore nearby Amherst and Northampton (less than 20 minutes away). Contactless self check-in and convenient parking makes your stay easy!

Top Guest favourite
A serene landscape features rolling hills blanketed in morning mist, with vibrant greenery in the foreground. Soft clouds hover above the distant mountains, creating a tranquil atmosphere that showcases the natural beauty of the Pioneer Valley.
Apartment in Amherst
5 out of 5 average rating, 55 reviews

The View Guest Suite - Amherst

Looking for the perfect place to stay in the five colleges area? The View Guest Suite - Amherst is now open and ready for you. Two luxurious King bedrooms and shower baths, full kitchen, dining area and living room for three non-smoking guests just minutes away from all of the action. Full lower floor in a newly built eco-friendly property, picture windows, spectacular views of the Pioneer Valley, your own decks, entrance and self check-in.

Guest favourite
A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.
Apartment in Holyoke
4.81 out of 5 average rating, 299 reviews

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.

Popular amenities for South Hadley holiday rentals