
Holiday rentals in Williamsburg
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Top-rated holiday rentals in Williamsburg
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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.
4.97 out of 5 average rating, 190 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!
4.99 out of 5 average rating, 444 reviews
Large Eco-friendly Studio – Walk to Town
★ Superhost for 12 years — a unique loft-style studio, surrounded by beautiful gardens, a short walk to town and Smith College. Perfect for visiting the colleges, attending weddings, workshops, or a peaceful stay away to work or write, close to hiking and bicycle trails. Before requesting a reservation, please send a quick message first. We respond fast to make sure the unique space is the right fit for you — we just like to say hello first! Read on to see if it sounds like your kind of stay.
4.93 out of 5 average rating, 308 reviews
1880s balconied luxury pad, best downtown location
Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.
4.91 out of 5 average rating, 251 reviews
Charming, updated , 3 bedroom farmhouse farm stay
Enjoy a tranquil stay on a small market farm. Winter is coming and we are midway between Berkshire East Ski Resort and the nightlife of Northampton. Plenty of great local cross country and snow shoe trails as well as snow mobile circuits and destinations. Dog-sledding! Enjoy beautiful evening skies while sitting around the fire pit. Mingle with the goats and ducks (duck eggs usually available) . Conveniently located to Northampton, Amherst, the 5 colleges, restaurants and family activity.
4.99 out of 5 average rating, 156 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!
4.98 out of 5 average rating, 312 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.
4.97 out of 5 average rating, 133 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.
4.99 out of 5 average rating, 230 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.
4.97 out of 5 average rating, 498 reviews
An 18th century farmhouse
Built in 1785 this antique Cape was carefully restored to its original design about 20 years ago. The house is set on a quiet road in the middle of fields, woods, gardens, and hiking trails. it is secluded with easy access to the natural world. The rooms are book-lined and filled with family objects. It is close to Berkshire East for skiing and snowboarding in the winter and whitewater rafting and swimming in the summer. Mass MoCA and the Clark Museum are within an easy drive.
4.97 out of 5 average rating, 110 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.
4.89 out of 5 average rating, 249 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.
4.99 out of 5 average rating, 276 reviewsPopular amenities for Williamsburg holiday rentals
Other great holiday rentals in Williamsburg

Down town Florence Temperance Hall
4.83 out of 5 average rating, 854 reviews
Private Studio for a Sweet Getaway!
4.98 out of 5 average rating, 172 reviews
Large Quirky Sunny Farmhouse Apartment
4.87 out of 5 average rating, 494 reviews
Hill-Ross Guest Suite
5.0 out of 5 average rating, 156 reviews
Retreat in the Woods
4.93 out of 5 average rating, 57 reviews
Beautiful 18th Century Farmhouse
5.0 out of 5 average rating, 41 reviews
Farmhouse on working dairy farm
4.98 out of 5 average rating, 65 reviews
Spacious, Sunny* Woodland Retreat
4.99 out of 5 average rating, 91 reviewsDestinations to explore
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- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Taconic State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Hudson Chatham Winery
- Dcu Center
- Ski Sundown
- Mount Monadnock
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Hancock Shaker Village





