Holiday rentals in Williamsburg

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Top-rated holiday rentals in Williamsburg

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Top guest favourite
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, 410 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
The spacious studio apartment features a well-equipped kitchen with a countertop and bar seating. Natural light filters through the windows, highlighting wooden cabinetry and modern appliances. The open layout includes a cozy seating area, creating a functional living space beneath sloped ceilings.
Flat in Williamsburg
4.96 out of 5 average rating, 146 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.

Top guest favourite
The entrance features a white door with a windowpane design, framed by light blue siding. A decorative lantern hangs beside the door. A small potted plant rests on a blue chair, while a welcome mat adorned with black dogs is placed at the threshold.
Guest house in Northampton
5 out of 5 average rating, 409 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
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 favourite
A historic farmhouse is set amidst lush greenery, with a well-maintained garden featuring colorful flowers. A sign invites visitors, while a vintage cart enhances the rustic charm. The surrounding landscape offers distant views of rolling hills under a partly cloudy sky.
Farm stay in Williamsburg
4.99 out of 5 average rating, 138 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.

Top guest favourite
The garden space is illuminated softly by warm lighting, creating a peaceful ambiance. A pathway winds through lush greenery, leading to a seating area surrounded by blooming flowers. Twinkling lights can be seen in the trees, enhancing the serene outdoor setting.
Guest suite in Williamsburg
4.98 out of 5 average rating, 292 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
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 favourite
A bright and spacious studio features a cozy futon couch in a rich purple hue, paired with a wooden coffee table. A small dining area is set with a flower vase, while angled ceiling adds character. A kitchenette area is visible in the background.
Home in Williamsburg
4.99 out of 5 average rating, 212 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
A modern dining area is shown with a wooden table set for six, accompanied by stylish gray chairs. In the background, a contemporary kitchen with sleek cabinetry and stainless steel appliances is visible, alongside a cozy living room featuring a comfortable sofa and a mounted television.
Flat in Northampton
5 out of 5 average rating, 139 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
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 van/Motorhome 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 favourite
A spacious studio apartment is presented, featuring a large bed with vibrant blue linens. Two bedside lamps flank the bed, providing balanced lighting. A small seating area with a teal couch and a neutral armchair is visible, complemented by decorative rugs on the wooden floor.
Flat in Williamsburg
4.89 out of 5 average rating, 235 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 favourite
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.
Flat in Northampton
4.99 out of 5 average rating, 229 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.

Popular amenities for Williamsburg holiday rentals