Holiday rentals 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
Guest suite in Northampton
4.98 out of 5 average rating, 283 reviews

Luxurious and Sunny Bedroom Suite!

Luxurious and sunny suite with private bath, separate entrance, Tv/sitting room, reading nook, desk/work area, and coffee bar. 6 blocks to town, and beautiful views of Skinner Mt. Decorated with handcrafted wood furniture by one of Northampton's most recognized furniture makers. Private patio, large backyard with pick-your-own raspberries and blueberries. The suite has a private parking space, and is conveniently located near the bike path, and route 91. Come relax, and explore Northampton.

Top guest favourite
A serene scene depicts several horses grazing in a fenced area, surrounded by vibrant autumn foliage. A charming white house is visible in the background, framed by trees under a clear blue sky. Natural light enhances the tranquil setting.
Guest suite in Belchertown
4.98 out of 5 average rating, 171 reviews

Serene 1-br suite on 75 acre horse property

Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

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, 309 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, 124 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, 67 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
The exterior of the tiny house is showcased, featuring a red wooden facade with white trim. A bright front door is framed by two small windows. Decorative potted plants and pumpkins are arranged along a stone pathway leading to the entrance.
Tiny home in Granby
4.99 out of 5 average rating, 70 reviews

Tiny House on Big, Pet-Friendly Farm

Cozy, clean 350sf tiny house on gorgeous farm. Enjoy the serenity of rural life, while being 15 minutes away from downtown Springfield and MGM Casino and 5-15 minutes away from all the local universities. Pet-friendly with a private yard and view you could look at all day. King-size bed, smart TV, electric fireplace, AC/heat and more! Tiny house rental includes the house, private yard and one parking space. If you’d like to utilize our larger fields, that can be reserved separately.

Guest favourite
The entrance features a covered porch with white railings, providing a welcoming pathway to the door. A potted plant with pink flowers is situated near the base of the stairs, adding a touch of greenery to the inviting entrance.
Home in Northampton
4.94 out of 5 average rating, 101 reviews

The Walnut Apartment

This beautiful and sunny 1 bedroom apartment is perfect for your stay in downtown Northampton, Massachusetts. It is walking distance to the Amtrak train station, all downtown restaurants and venues. Perfect for a stay to visit Smith College. You will find the beautiful claw foot tub perfect for relaxing after a day spent in the beautiful Pioneer Valley. This fully furnished apartment has a full kitchen, full bathroom, new furnishing, queen sized bed and its own entrance.

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.
Flat 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.
Flat in Northampton
4.99 out of 5 average rating, 256 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, 171 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.
Flat in Amherst
5 out of 5 average rating, 57 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.

Popular amenities for South Hadley holiday rentals