Vacation rentals in Williamsburg

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Top-rated vacation rentals in Williamsburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 272 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!

Mar 10 – 17

G$25,185 GYD per night

Guest favorite

Guest suite in Williamsburg

4.98 out of 5 average rating, 230 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!

Nov 25 – Dec 2

G$26,399 GYD per night

Guest favorite

Guest suite in Sunderland

5.0 out of 5 average rating, 143 reviews

Bright private suite minutes to Five College area

Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Café. Suite is professionally cleaned between each stay.

Aug 29 – Sep 5

G$18,983 GYD per night

Guest favorite

Barn in Northampton

4.95 out of 5 average rating, 541 reviews

E. Slate Carriage House

A private, comfortable studio in a converted 1890's Carriage House. Five minute walk to the center of "Noho." Close to cafes, events, public transportation, shops, Smith College. Reserved parking, private entrance. Efficient kitchen, laundry, a large shower, AC/Heat. Wifi, coffee/tea provided. No shared walls. You may hear footsteps if there is a guest staying in the 2nd floor. No road or pedestrian noise. 1-Queen bed (bed is new in 2024). No TV. Studio is about 430 sq. Great Location.

Oct 14 – 21

G$28,827 GYD per night

Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 157 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.

Dec 25 – Jan 1

G$25,688 GYD per night

Guest favorite

Apartment in Leeds

4.99 out of 5 average rating, 114 reviews

Private Studio for a Sweet Getaway!

We offer a cozy, comfortable, studio apartment located in the heart of the Pioneer Valley right on the bike path, a walk to Look Park and easy access to hiking. We are a 10 minute drive to downtown Northampton with lots of great restaurants and music. Our proximity to Snow Farm, Smith and the other area colleges makes this an ideal overnight spot for parents in town for a brief visit, people attending area workshops and classes or for those looking to stay longer and explore the area.

Nov 15 – 22

G$28,518 GYD per night

Superhost

Yurt in Williamsburg

4.87 out of 5 average rating, 174 reviews

magical yurt in the woods. long term discount

sweet cozy yurt nestled in the woods, surrounded by watershed land, wonderful trails. Magical, quiet, on a dirt road, no street lights. Perfect for retreat, unplugged time, your creative down time, Private yet not isolated, starry nights, owls, full kitchen, private entrance to private bathroom in the main house 200 ft away from the yurt. Wood heat, must be comfortable with a wood stove chop wood/carry water mentality( wood already chopped. A little piece of timeless heaven.

Nov 27 – Dec 4

G$18,161 GYD per night

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 238 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Mar 1 – 8

G$24,805 GYD per night

Guest favorite

Apartment in Williamsburg

4.87 out of 5 average rating, 181 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.

Jun 24 – Jul 1

G$27,011 GYD per night

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 350 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, full kitchen, and bathroom (with tub but no shower). The studio has an open floor plan including a front room with twin bed and a smaller TV room with futon sofa that can open into a double bed. 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.

Oct 6 – 13

G$20,302 GYD per night

Guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 646 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Nov 30 – Dec 7

G$22,230 GYD per night

Guest favorite

Apartment in Northampton

4.96 out of 5 average rating, 278 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Modern cozy 1BR with living space, private bathroom, private driveway, screened porch, coded door, and inflatable hot tub! Wooded neighborhood. Bike path along river. 5 min. drive to Look Park. 10 min. drive to Northampton. BR has luxury queen bed, single bed, AC. Cozy LR, WiFi, 55" TV, equipped kitchen. Near excellent hikes. A family lives in attached unit so there is some noise, not during sleep hours. Cats have lived here in the past. Great getaway spot!

Sep 25 – Oct 2

G$27,609 GYD per night