Vacation rentals in Westhampton

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Top-rated vacation rentals in Westhampton

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Guest favorite

Cabin in Chesterfield

4.91 out of 5 average rating, 116 reviews

The Glow Room at Indian Hollow

The Glow Room at Indian Hollow is a history-rich 1850 post & beam barn, renovated in a light-filled, post modern style. Imagine getting out of your car, opening the screen door to a big porch that overlooks a leaping mountain brook, deep enough to dunk in. Then pass through the strap-hinged front door and into a glowing pine-panelled great room with giant windows, a big wood stove, 3 Chesterfield couches, dining area and kitchen. You see the forest all around you, but you're inside, ready to unwind. Upstairs, the loft features the master bedroom (sleeps 2, queen) and a reading/games room (can sleep 2, futon). Walking into the ell, you pass the bathroom, the 'room with no purpose,' and the guest bedroom (sleeps 2, futon) which opens onto the back deck, where the barbecue is, and the sound of the leaping waters. In summer the lawn is thick and lush, and you are surrounded with pines, birches, maples and mountains. Chauncey Brook forms the east border & offers a serene and ferny welcome; overlooking it, there's a beautiful firepit surrounded by log benches. The southern border is the Dead Branch Brook with its refreshing plunge pools. About a 1/4 mile downstream it joins the East Branch of the Westfield River, a federally-designated 'Wild and Scenic River.' We will provide you with maps and information about the area, which contains extraordinary opportunities for picnicking, fishing, hiking, biking, swimming, x-country skiing, snow-shoeing, photography and painting. And being alone, with someone you want to be alone with. This property is designed to inspire the maximum enjoyment of the 15+ square miles of open space that begins at its doorstep. The Glow Room is a launching pad. To amplify the quiet and help you unplug, there is no internet service (bring DVDs for your laptop). New cell phones work, but will drop out.

Top guest favorite

Apartment in Leeds

4.98 out of 5 average rating, 155 reviews

Private Studio for a Sweet Getaway!

A cozy, comfortable, studio flat with ready access to local music venues and restaurants. Downtown Northampton is 15 mins by car or a 1/2 hr bike ride. We abut the bike path and there's a Valley Bike Share kiosk nearby. Ideal overnight spot for visiting Smith and other area colleges or for attending workshops at Snow farm. Easy day trips the Berkshires. Plenty of area hiking! Perfect personal retreat spot! I accept dogs on a case by case basis, small dogs preferred and I cannot accept cats.

Guest favorite

Guest suite in Northampton

4.87 out of 5 average rating, 557 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

Guesthouse in Cummington

5 out of 5 average rating, 106 reviews

Clark Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Guest favorite

Cabin in Cummington

4.98 out of 5 average rating, 220 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Top guest favorite

Guest suite in Williamsburg

4.98 out of 5 average rating, 269 reviews

Happy Maples!

I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

Guest favorite

Guest suite in Easthampton

4.92 out of 5 average rating, 269 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 favorite

Home in Williamsburg

4.99 out of 5 average rating, 194 reviews

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

Top guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 373 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

Camper/RV in Westhampton

4.89 out of 5 average rating, 177 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.

Guest favorite

Apartment in Williamsburg

4.88 out of 5 average rating, 216 reviews

Studio apartment on route 9, "Inn the Valley"

A bright and cozy studio apartment on PVTA bus line just outside of Northampton, MA. Skylight, wood floors, kitchen, and full bathroom as well as heat and air conditioning, oriental rugs and unique furnishings. 10 minutes from Northampton center and 20 minutes from Amherst center. Very convenient for all 5 colleges. Five minutes from Snow Farm Art Institute. Two minutes from Valley View Farm. We are meticulous in our cleaning and disinfecting in the face of Covid-19.

Top guest favorite

Guest suite in Easthampton

4.96 out of 5 average rating, 450 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.