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Search Holiday Homes in Williamstown

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Browse Select Williamstown Holiday Homes

Honeysuckle Rose Cottage
173 Barker Rd, Pittsfield, MA
Situated in Pittsfield, this holiday home is within 2 miles (3 km) of Colonial Theater, Berkshire Museum and Berkshire Athenaeum. Housatonic River and Canoe ...
4.5/5Wonderful! (2 reviews)
Quaint and Beautiful Little Cottage
"We loved staying here! It was quaint and relaxing, just what we wanted. Despite the age of the cottage the heaters throughout kept us nice and warm. We were cozy the whole time. Some great books to read on the shelves and the TV was set up with streaming services and cable. Not a far drive from trails ..."

Reviewed on 11 Mar 2021

Honeysuckle Rose Cottage
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!
Situated in Williamstown, this holiday home is 2.1 mi (3.4 km) from Jiminy Peak Mountain Resort and within 6 miles (10 km) of Pittsfield State Forest and Mount ...
5/5Exceptional! (6 reviews)
A lovely relaxing stay
"We had such a nice time. It was great being able to just relax in front of the fire place for a couple days. Very peaceful."

Reviewed on 7 May 2021

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!
New! Lakeside Berkshires Home Near Hiking & Skiing
Situated in Lanesborough, this property is within 6 miles (10 km) of Pittsfield State Forest, Jiminy Peak Mountain Resort and Mount Greylock State Reservation. ...
New! Lakeside Berkshires Home Near Hiking & Skiing
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The Gatehouse on Golden Hill
117 Golden Hill Rd, Lee, MA
Situated in Lee, this holiday home is within 2 miles (3 km) of Animagic Museum of Animation, Lee Library and Housatonic River. Greenock Country Club and Wood's ...
4.9/5Exceptional! (26 reviews)
Week in the Berkshires
"Four generations of my family were more than comfortable for a week at the Gatehouse at Golden HIll. Our group ranged in ages from 18 months to 88 years. The space worked perfectly and the location is central to everything. Teva, our house could not have been more attentive. He responded to any need ..."

Reviewed on 15 Jul 2021

The Gatehouse on Golden Hill
Dancing Horse Lodge
191 Tamarack Rd, Pittsfield, MA
Situated in the mountains, this holiday home is within 3 miles (5 km) of Housatonic River, Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe ...
4.3/5Excellent! (7 reviews)
"Very Nice Location. Comfortable accommodations"

Reviewed on 25 Jul 2021

Dancing Horse Lodge
Enchanting Forest Hide-away
58 Robinson Hollow Way, Stephentown, NY
Located on the riverfront, this family-friendly holiday home is within 9 mi (15 km) of Cherry Plain State Park, Pittsfield State Forest and Jiminy Peak Mountain ...
5/5Exceptional! (4 reviews)
Weekend with old friends
"Very private with lovely outdoor settings including a beautiful garden. Comfortable common rooms with great chairs for reading and relaxing. Kitchen was well-equipped. Bedrooms were comfortable. Owner was very responsive and communicative."

Reviewed on 17 Jul 2021

Enchanting Forest Hide-away
Wilmington / Mt. Snow/ Chimney Hill Southern Vermont Home
This family-friendly Wilmington holiday home is within 2 mi (3 km) of Deerfield River, Deerfield River and Jim McGrath Gallery and Studio. The Hermitage Golf ...
3/5 (9 reviews)
SCAM, DO NOT BOOK, NOT A REAL RENTAL
"I am astounded how terrible this owner and VRBO are. This is a scam set up to steal your money. If you book the owner will not respond to your messages. VRBO will not help you. This house is abandoned. It hasn’t been mowed in years. There is no running water. There is moldy food in the refrigerator. ..."

Reviewed on 18 Jul 2021

Wilmington / Mt. Snow/ Chimney Hill Southern Vermont Home
Walk to Village of Lenox two Blocks Away ! Home Away From Home
Located in the mountains, this Lenox holiday home offers ski-in/ski-out access within 1 mile (2 km) of Lenox Library, Ventfort Hall Mansion and Gilded Age Museum ...
5/5Exceptional! (21 reviews)
Impeccable
"April is a terrific host. As others have said, this place is spotless and well-equipped, and the knives are even sharp, unlike most short-stays. We loved the location so much that we considered buying the house!"

Reviewed on 17 Jul 2021

Walk to Village of Lenox two Blocks Away ! Home Away From Home
General Williams Estate House Lenox/stockbridge
This family-friendly Stockbridge holiday home is within 3 mi (5 km) of Berkshire Theatre Festival, Berkshire Botanical Garden and Greenock Country Club. Housatonic ...
4.8/5Exceptional! (62 reviews)
Beautiful property
"Celebration of friends for over forty years. Twelve women and house accommodated us beautifully. Beds were extremely comfortable. Great house, great location and great hosts."

Reviewed on 15 Jul 2021

General Williams Estate House Lenox/stockbridge
Berkshires Waterfront Lakehouse
141 Old State Rd, Lanesborough, MA
Situated on the waterfront, this holiday home is within 6 miles (10 km) of Mount Greylock State Reservation, Jiminy Peak Mountain Resort and Mount Greylock State ...
4.7/5Exceptional! (54 reviews)
Good get out of the city location
"Rustic. Lots of bird life. Well stocked Kitchen"

Reviewed on 25 Jul 2021

Berkshires Waterfront Lakehouse
19th c. Renovated Barn in the Berkshires
195 W Mountain Rd, Cheshire, MA
This family-friendly Cheshire holiday home is located in a rural location, 1.2 mi (2 km) from Mount Greylock State Reservation, and within 6 mi (10 km) of Topia ...
4.7/5Exceptional! (35 reviews)
Stunning location and accommodations.
"The barn was beyond beautiful and it was a treat for our family to stay in such an interesting and comfortable space. It was spotless, had very comfortable beds, a well appointed kitchen, great books and was perfect for a relaxing long weekend. Great hiking at Greylock is just down a dirt road and ..."

Reviewed on 15 Jun 2021

19th c. Renovated Barn in the Berkshires
Lovely Chalet at Chimney Hill Resort Community,
3 Fox Mountain Road, Wilmington, VT
This family-friendly Wilmington resort is located in the mountains, within 3 mi (5 km) of Warlock's Woods, Enchanted Forest Ski Run and Secret Passage. Deerfield ...
5/5Exceptional! (32 reviews)
Chimney Hill in Wilmington Vt.
"Great location, clean house with all necessary kitchen amenities; micro, toaster, Keurig coffee maker, granite countertop. Large frig with ice maker. Plenty of Hot water in bathrooms and kitchen. House heats up quickly, and wood stove lights easily and adds a nice comfy feeling."

Reviewed on 23 Feb 2021

Lovely Chalet at Chimney Hill Resort Community,
2 Bedroom Newly Renovated Townehouse, Beautifully Decorated at Garfield House
Located in the heart of Lee, this holiday home is within a 5-minute walk of Animagic Museum of Animation, Lee Library and Housatonic River. Greenock Country ...
4.8/5Exceptional! (12 reviews)
First Timer to the Berkshires
"A wonderful two story townhouse in a great location. Easy to walk around the town of Lee and easy to get to nearby towns as well via the "main drag." Host was proactive in offering to install the AC window unit prior to an unexpected heat wave. Nice patio area for sitting outside and enjoying the ..."

Reviewed on 4 Jul 2021

2 Bedroom Newly Renovated Townehouse, Beautifully Decorated at Garfield House
New! Peaceful Family Home w/ Fire Pit & Large Yard
Situated in Williamstown, this property is 1.9 mi (3 km) from Hopkins Observatory and 1.9 mi (3.1 km) from Williams College. Williams College Museum of Art and ...
5/5Exceptional! (1 review)
Beautiful Home - Perfect Location
"House was beautiful. Kitchen was fully stocked and extremely well organized. Great restaurants and other attractions including The Clark Museum within a 10 mile radius. We will return!"

Reviewed on 27 Jul 2021

New! Peaceful Family Home w/ Fire Pit & Large Yard
Blissful Summer....
68 Old Stockbridge Rd, Lenox, MA
Located in the centre of Lenox, this family-friendly holiday home is within a 15-minute walk of Lenox Library and Ventfort Hall Mansion and Gilded Age Museum. ...
5/5Exceptional! (39 reviews)
Wedding weekend w/ friends
"My friends and I stayed at Pegs for a quick wedding weekend. It was perfect for our small group but everyone was still able to have their own personal space. The screened in porch was probably our it favorite place to hang out and it was just a short walk to town! If I find myself in Lenox again ..."

Reviewed on 3 Jul 2021

Blissful Summer....
Highland House
719 NW Hill Rd, Pownal, VT
Located on the riverfront, this family-friendly holiday home is within 6 mi (10 km) of Williamstown Trailhead, Hopkins Observatory, and Williams College. 62 ...
5/5Exceptional! (1 review)
Fourth of July
"The perfect place for family to unwind after my daughter’s wedding! Spectacular property and well appointed home. We all loved it and will go back!"

Reviewed on 7 Jul 2021

Highland House
Star Gazer Farm
315 Garfield Rd, East Nassau, NY
Situated in East Nassau, this holiday home is 7.7 mi (12.3 km) from New Lebanon Library and 10.6 mi (17.1 km) from Pittsfield State Forest. Jiminy Peak Mountain ...
5/5Exceptional! (1 review)
"Self-contained apartment with private entrance adjacent to owner’s farmhouse: large, antique-filled living/dining room, well-equipped kitchen, full bath with lovely shower, loft double bedroom upstairs, gorgeous swimming pool & tennis court on the grounds. Very special place, and owner Christine, ..."

Reviewed on 18 Jul 2021

Star Gazer Farm
Home in the Berkshires
67 Jericho rd, Williamstown, MA
Located in Williamstown, this family-friendly holiday home is 1.6 mi (2.6 km) from Jiminy Peak Mountain Resort, and within 6 mi (10 km) of Pittsfield State Forest ...
4.9/5Exceptional! (17 reviews)
Great Stay
"The home was clean, spacious, and cozy. The owners were super communicative if/when we reached out. The checkin and checkout were well communicated and easy. Kitchen and bathrooms were well stocked. And it was 5 minutes to Jiminy Peak, which was an added bonus. We would definitely stay here again. ..."

Reviewed on 21 Feb 2021

Home in the Berkshires
Cozy 1 Bedroom Farm Stay Cottage
4.3/5Excellent! (3 reviews)
Hiking in the Green Mountains
"We stayed at the Cloud Compound for 3 nights. What a perfectly sized little space for two hikers. The accommodations were very comfortable and perfect to come back to after a long day of hiking/ice fishing/ winter activities. And there were fresh eggs in the fridge! Thank you!"

Reviewed on 4 Mar 2021

Cozy 1 Bedroom Farm Stay Cottage
Cozy Converted Barn on Secluded 6.5 Acres
78 Broken Pines, Bennington, VT
This family-friendly Bennington holiday home is located in a rural location, within 3 mi (5 km) of Robert Frost Stone House Museum, Howard Park and Park McCullough ...
5/5Exceptional! (92 reviews)
In the middle of no where
"So peaceful. The dogs loved being off leash, a totally rare treat for them. Very quiet. Stayed a week and didn't want to leave."

Reviewed on 25 Jun 2021

Cozy Converted Barn on Secluded 6.5 Acres
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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 property types in Williamstown

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is £280 per night from 10 Aug to 10 Aug
4.8/5Exceptional! (110 reviews)
"Rooms are beautiful, spacious, clean. It's a beautiful property. Our one complaint is the barn doors on the bathroom are a very nice touch, aesthetically speaking, but EVERY sound made in the bathroom can be heard throughout the room. EVERY SOUND! And because of the acoustics in the bathroom, it's ..."

Reviewed on 24 Jul 2021

The Williams Inn
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 out of 5
430 Main St, Williamstown, MA
The price is £125 per night from 16 Aug to 16 Aug
4.3/5Excellent! (67 reviews)
"Friendly staff and clean rooms"

Reviewed on 26 Jul 2021

Fairfield Inn & Suites by Marriott Williamstown
The Villager Motel

The Villager Motel

2 out of 5
953 Simonds Rd, Rt 7 North, Williamstown, MA
The price is £60 per night from 1 Aug to 1 Aug
4/5Very Good! (287 reviews)
"Very comfortable beds"

Reviewed on 26 Jul 2021

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.

Williamstown Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in Williamstown?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in Williamstown?

Choose from 100 beautiful holiday homes in Williamstown for your getaway.


How much is a holiday home in Williamstown?

You can find perfect holiday homes in Williamstown for as low as £60 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in Williamstown?

Find the best deals on Williamstown holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in Williamstown?

There’s no better way to spend your well-earned holiday than in a private, cosy Williamstown holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Williamstown.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Williamstown holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Williamstown—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Williamstown car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

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