Holiday houses in South Hadley

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Top-rated holiday rentals in South Hadley

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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, 115 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.

Guest favourite
Apartment in Amherst
4.91 out of 5 average rating, 243 reviews

1840 restored beauty in the best downtown location

Newly restored 2nd-floor apartment in 175-year-old home 2 blocks from Amherst Cinema & steps to everything this vibrant downtown has to offer. Walking distance to Amherst College and UMass. This home retains the character of days gone by, yet sparkles with new wood floors, modern bathroom & new appliances. Original wood-paneled entry hallway & exposed beams throughout. Antique furnishings, historic wall decor, and a sunny kitchen with built-in reclaimed wood bar. Small balcony w seating for 2.

Top Guest favourite
A sliding barn door reveals a cozy sleeping area featuring a spacious bed with neutral bedding. A small lamp sits atop a bedside table, and a chest of drawers adds functionality. Light enters through a window adorned with blinds, creating a warm ambiance.
Guest suite in Northampton
4.87 out of 5 average rating, 598 reviews

Separate apt, 1 mile from downtown, 1 guest only

This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Guest favourite
A decorative sign featuring an anchor design and the text 'Luke & Ali Riverfront' is displayed prominently. The sign is octagonal and metallic, contrasting with the lush green landscape in the background.
Guest suite in South Hadley
4.84 out of 5 average rating, 132 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails l

Guest favourite
A warm, orange wall frames the sleeping area, featuring a spacious bed with neutral linens and decorative pillows. Soft light is provided by two bedside lamps, and a large window offers a glimpse of the outside while inviting natural light into the room.
Apartment in Northampton
4.94 out of 5 average rating, 117 reviews

Warm & Stylish Apartment w/laundry - walk to DT

Warm and stylish 1 bedroom apartment with private garden entrance located steps from downtown Northampton. Newly refinished with a comfortable queen bed, sleeper sectional and luxury linens. It has a fully functional kitchen, bathroom, living room with a flatscreen, Roku and high-speed wifi as well as a washer/dryer in the unit-- perfect for a staycation or for a relaxed homestay for your remote work. Walk 15 mins to restaurants downtown, 20 mins to Smith College and 2 to the bike path.

Top Guest favourite
A panoramic view of the expansive farmland stretches towards a distant mountain range under a colorful twilight sky. Two wooden chairs are positioned on the grassy area, providing a serene spot to enjoy the landscape.
Tiny home in Northampton
4.98 out of 5 average rating, 264 reviews

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Top Guest favourite
A vibrant red and orange tree stands beside a deep red building, showcasing the beauty of autumn foliage. The tree's colorful leaves contrast with the clear blue sky, while a parked car is visible in the foreground, adding to the peaceful residential atmosphere.
Barn in Northampton
4.97 out of 5 average rating, 659 reviews

Brookside Carriage House. Private, Great Location.

1890's Carriage House. Bright 850 sq. ft., 2nd flr. studio. Original wood flrs, 12' ceiling, skylights, modern amenities w/ rustic charm. Onsite parking. Two sleeping nooks: One QUEEN, One FULL bed & a leather couch; open floor plan. Shower, laundry, full kitchen, dining table, lounging area, Juliet balconey. Eclectic, spacious, private, quiet, all in a fantastic location. This is a large studio. Staircase to 2nd floor. No TV. Dog friendly; contact me first. Non-Smoking/vaping.

Top Guest favourite
A living room features a spacious leather sofa facing a large wall-mounted TV and a modern electric fireplace. A built-in shelf holds a collection of books. Soft lighting creates a comfortable ambiance, with a view of the dining area and window in the background.
Home in Northampton
4.98 out of 5 average rating, 195 reviews

Modern Comfort Meets Northampton’s Vibrant Charm

Experience the Best of Northampton! From vibrant nightlife to tranquil retreats, Northampton has something for everyone, and our newly renovated, two-bedroom duplex puts you right at the center of it all. Whether you’re catching live music, indulging in farm-to-table dining, or browsing unique local shops, every adventure is just steps away. Book your stay today and experience the perfect balance of comfort, convenience and charm in one of Northampton’s most highly rated homes!

Top Guest favourite
A spacious studio is illuminated by natural light from large windows. The bright room features a mix of furnishings, including a white sofa, a dining table, and a variety of shelving units. Warm wood flooring complements the inviting layout.
Guesthouse in Northampton
4.93 out of 5 average rating, 291 reviews

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

Top Guest favourite
A vibrant red living room features large windows overlooking a wooded area, allowing natural light to filter in. The seating consists of plush gray sofas and armchairs, complemented by a red coffee table adorned with decorative items. A vintage wardrobe sits against the wall.
Guest suite in Easthampton
4.96 out of 5 average rating, 474 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
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
4.91 out of 5 average rating, 285 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.

Superhost
An organized living space features a spacious bed centered against the wall, accompanied by a dark sofa with decorative cushions. A media console holds a television, with built-in shelves displaying plants and framed art. Soft lighting enhances the warm wood flooring.
Guest suite in Holyoke
4.83 out of 5 average rating, 260 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!

Popular amenities for South Hadley holiday rentals

Frequently Asked Questions

  • What are the most popular amenities for House Rentals in South Hadley?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there house rentals with a dedicated workspace in South Hadley?

    Yes! Work meets play with ease at over 10 house rentals in South Hadley featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in South Hadley?

    Make yourself at home in South Hadley by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in South Hadley Falls, and over 40 vacation rentals in Highlands.

  • How much does it cost to stay in house rentals in South Hadley?

    Experience the best of South Hadley with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in South Hadley have free parking?

    Absolutely! We offer over 10 house rentals with free parking in South Hadley. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in South Hadley have wifi?

    Absolutely! We offer over 10 house rentals with wifi in South Hadley. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in South Hadley?

    South Hadley has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in South Hadley have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in South Hadley. Enjoy a tailored experience with all the comforts you desire.