Williamstown Holiday Rentals

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Holiday Rentals in Williamstown

Property grounds
Simple and Elegant 19th Century Williamstown Home
9.4 out of 10, Exceptional, (8)
"We did not stay at this property, we were moved to another location, I think due to scheduling. The coordinator was very responsive and the other location was beautiful. We had a wonderful stay and would work with these folks again in the future."
The price is NZ$833
includes taxes & fees
25 May - 26 May
Simple and Elegant 19th Century Williamstown Home
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is NZ$280
includes taxes & fees
29 May - 30 May
Jiminy Peak Mountain Resort
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (13)
"Had such a wonderful stay in the beautiful Berkshires at this unique cabin property! Everything was clean and well-maintained. Very rustic and charming. We had a lot of fun by the fire and walking down to the river in the backyard. So many things to do in this area! Hiking, rafting, and dining in the nearby towns! Would definitely return!"
The price is NZ$990
includes taxes & fees
6 Jun - 7 Jun
Bear Creek Cabin
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
1 bedroom, WiFi, bed sheets
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (116)
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
View from property
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (97)
"Lovely chalet by the lake, we had such a relaxing stay. The place is just like on the pictures, very quiet but not far from amenities. The host are very friendly super responsive. Thanks for having us!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Pool
Mountainside Condo Ski In Ski Out
8.8 out of 10, Excellent, (8)
"Great location and nice unit. Had a blast!"
The price is NZ$306
includes taxes & fees
27 May - 28 May
Mountainside Condo Ski In Ski Out
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Exterior
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, (79)
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (35)
"Amazing House, so much character. More than enough room for large family meals and gatherings. My family really enjoyed it. Having no snow was a disappointment, but we will try again another year. Thank you"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (64)
"This is the 2nd time we've stayed here and loved it again. This has become our go to place to stay for our Berkshires adventures. Clean, comfortable, beautiful, private (the garden center was not open while we were there in Feb.), and great location!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
10.0 out of 10, Exceptional, (149)
"Our family absolutely loved our stay! We all commented that we would love to one day live in a place like this! :-) Gorgeous home (clean & welcoming) and gorgeous wooded area (loved sitting by the babbling brook)!!! Overall wonderful, relaxing experience. Would come back in a heart beat!"
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
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See all available properties in Williamstown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Williamstown you may be interested in

Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (294)
"Love the Williams Inn"
The price is NZ$483
includes taxes & fees
27 May - 28 May
The Williams Inn
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (270)
"Cleanliness. Conenience. Lobby decor. Friendly service. Late model hi def TV. Comfy bed."
The price is NZ$295
includes taxes & fees
29 May - 30 May
Fairfield Inn & Suites by Marriott Williamstown
Exterior
The Villager Motel
2.0 star property
8.8 out of 10, Excellent, (595)
"The room was great, clean and neat. There was a chemical odor in the room, we actually rented two rooms and they both had an odor. I am unable to identify, other than to think it was some sort of chemical odor. I got some fabreeze to help. Friendly staff on check in."
The price is NZ$145
includes taxes & fees
30 May - 31 May
The Villager Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Williamstown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Williamstown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Williamstown. Seeing all the best attractions is bound to make you fall in love with Williamstown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Williamstown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Williamstown?

Yes, there are holiday rentals in Williamstown close to Hopkins Observatory, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the university campus and art scene in Williamstown. You can also check out the museums while you're visiting.

What are some of the best holiday rentals that Williamstown has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Williamstown is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Williamstown?

Choose from 29 Expedia holiday rentals in Williamstown for a memorable holiday.

What can I see and do in Williamstown?

Cultural attractions include Sterling and Francine Clark Art Institute and Williamstown Theatre Festival, whereas Mount Greylock State Reservation and Brodie Mountain are a couple of picturesque spots to enjoy the outdoors. While here, The Clark Art Institute and Williams College Museum of Art are other places worth a visit.

What are holiday rentals like in Williamstown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Williamstown. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.

Recent reviews of Williamstown properties
Expedia verified reviews