Holiday houses in Williamsburg

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Top-rated holiday rentals in Williamsburg

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Top Guest favourite
Guest suite in Northampton
4.88 out of 5 average rating, 401 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 favourite
Apartment in Williamsburg
4.95 out of 5 average rating, 117 reviews

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Guest favourite
Apartment in Conway
4.98 out of 5 average rating, 106 reviews

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the local ski resort Berkshire East. There are many sights, country roads, trails to explore, along with many varied excellent restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Top Guest favourite
Guesthouse in Northampton
4.99 out of 5 average rating, 377 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Top Guest favourite
Farm stay in Williamsburg
4.98 out of 5 average rating, 126 reviews

Charming, updated , 3 bedroom farmhouse farm stay

Enjoy a tranquil stay on a small farm. Enjoy sunrises across the fields and rolling hills while sipping your morning coffee. Enjoy beautiful evening skies while sitting around the fire pit. Mingle with the goats and ducks (fresh duck eggs are usually available for purchase). Conveniently located to Northampton, Amherst, the 5 colleges, restaurants and family activity. We are right next door to Snows Craft Farm and a few miles from Valley View Farm, Quonquont Farm and Look Park Concerts!

Top Guest favourite
Guest suite in Williamsburg
4.98 out of 5 average rating, 280 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!

Top Guest favourite
Cabin in Williamsburg
4.97 out of 5 average rating, 111 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.

Guest favourite
Tiny home in Northampton
4.98 out of 5 average rating, 239 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
Home in Williamsburg
4.99 out of 5 average rating, 207 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 favourite
Apartment in Northampton
5 out of 5 average rating, 118 reviews

Gorgeous Getaway

Brand new construction and state-of-the-art styling make this first-floor apartment a one-of-a-kind masterpiece. Every detail has been meticulously planned to ensure your visit is memorable! Just minutes from downtown Northampton, this stunning apartment features a spacious king-size bedroom with a private bath that includes a beautifully tiled walk-in shower, a second queen-size bedroom, a gorgeous kitchen with quartz countertops, and a beautiful living room with a flameless fireplace.

Guest favourite
Apartment in Northampton
4.97 out of 5 average rating, 401 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.

Top Guest favourite
Apartment in Williamsburg
4.88 out of 5 average rating, 224 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.

Popular amenities for Williamsburg holiday rentals