Vacation rentals in Westhampton

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Top-rated vacation rentals in Westhampton

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Top guest favorite
An open studio space is featured, showcasing a dining table with two chairs beside a kitchenette. A door leads to the outside, and walls display framed artwork. Light wooden floors complement the bright atmosphere of the room, which includes a twin bed and a side console.
Guest suite in Northampton
4.88 out of 5 average rating, 409 reviews

Cheery artist's studio in Florence

This 2nd floor guest suite in my home has a private entrance via an outdoor set of stairs (See Guest access section for details), full kitchen, and bathroom (tub but no shower). The open floor plan includes a front room with twin bed and a smaller TV room with futon sofa that I convert to a double bed as needed. Originally my art studio, I now offer it for short-term stays. COVID-19 policy. I allow 24 hours between bookings (no same-day turnovers). I request that my guests be fully vaccinated.

Top guest favorite
Guest suite in Village of Pelham
4.99 out of 5 average rating, 150 reviews

Refined cozy studio retreat – Under the Hemlocks

Escape to a tranquil boutique‑style studio guest suite under the hemlocks — a refined bijou space, small in scale yet elegantly detailed and entirely your own. Sink into the dreamy bed, soak in the deep clawfoot tub, venture to the unique off‑grid Writer’s Retreat, or steal a quiet moment in the private courtyard. Elegant furnishings, fine linens, a bespoke kitchenette, and curated amenities create a serene haven — minutes to Amherst Center, Amherst College, UMass, and the Emily Dickinson Museum

Top guest favorite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 461 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favorite
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, 600 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.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 352 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.
Loft in Tolland
4.96 out of 5 average rating, 323 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Top guest favorite
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, 116 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 favorite
The image features a scenic view of a sunset, casting vibrant hues across a cloudy sky. Lush green fields extend into the distance, bordered by farm buildings and trees. The tranquil atmosphere highlights the open farmland typical of the Hadley area.
Apartment in Hadley
4.97 out of 5 average rating, 267 reviews

Sweet Retreat minutes from Northampton & Amherst

Our home is in Hadley, MA which is less than 5 minutes from Amherst and 10 minutes from Northampton. Amherst is home to the flagship campus of University of Massachusetts, Amherst College and Hampshire College. Northampton is home to Smith College and in nearby South Hadley is the campus of Mount Holyoke College. Hadley is known for it's farmlands and open spaces. Northampton is a vibrant arts community that overflows with great restaurants, shops, cafes, music venues and galleries.

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, 438 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.

Guest favorite
The kitchen area features a light countertop with modern cabinetry and a stylish backsplash. A coffee maker, dish drying rack, and sink are visible. Organized jars hold various kitchen supplies, creating a functional and tidy space for meal preparation.
Camper/RV in Westhampton
4.9 out of 5 average rating, 223 reviews

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Top guest favorite
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, 225 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.

Top guest favorite
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
4.94 out of 5 average rating, 159 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!

Popular amenities for Westhampton vacation rentals