Williamstown Holiday Rentals

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Our top choices for Williamstown holiday rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2194)
"I great place to stay!!"
United Kingdom
Maricel
The price is NZ$219
includes taxes & fees
11 Jan - 12 Jan 2026
Vacation Village in the Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$390
includes taxes & fees
11 Jan - 12 Jan 2026
Huttopia Berkshires

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is NZ$590
includes taxes & fees
6 Jan - 7 Jan 2026
BLUSH: Boutique TINY home*private spa*walk to town

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is NZ$623
includes taxes & fees
12 Jan - 13 Jan 2026
Sugar Shack - 300 square feet of pure sweetness.

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is NZ$713
includes taxes & fees
13 Jan - 14 Jan 2026
HunnyHAUS: Deluxe TINY*private spa*walk to town

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is NZ$409
includes taxes & fees
11 Jan - 12 Jan 2026
Jiminy Peak Mountain Resort

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is NZ$420
includes taxes & fees
3 Jan - 4 Jan 2026
Berkshires Apartment at the Stephentown Hotel

Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is NZ$316
includes taxes & fees
1 Jan - 2 Jan 2026
Taborton Harvest Timber Trails Unique cabin experience

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is NZ$525
includes taxes & fees
2 Jan - 3 Jan 2026
Lake Whitingham & Mount Snow Area Village Apartment

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is NZ$628
includes taxes & fees
4 Jan - 5 Jan 2026
Florida Mountain Log Cabin

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is NZ$356
includes taxes & fees
2 Jan - 3 Jan 2026
Charming Apt in 18th c Berkshire Farmhouse

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is NZ$421
includes taxes & fees
2 Jan - 3 Jan 2026
Penthouse Apartment on Park Street

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is NZ$770
includes taxes & fees
5 Jan - 6 Jan 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is NZ$630
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (100)
"Beautiful, serene location with great penned in area for my lovable, niece pup! Spacious house with all the key amenities. Easy access for my elederly mom. "
United States
Lynn F.
The price is NZ$530
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,031
includes taxes & fees
11 Jan - 12 Jan 2026
Bear Creek Cabin

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Whitingham
10.0 out of 10, Exceptional, (14)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is NZ$1,068
includes taxes & fees
12 Jan - 13 Jan 2026
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is NZ$636
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is NZ$668
includes taxes & fees
11 Jan - 12 Jan 2026
UNIQUE - 1BR Country Condo @ Jiminy Peak

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is NZ$727
includes taxes & fees
3 Jan - 4 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
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.
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Top Williamstown Hotel Reviews

Find out more about Williamstown

Everything you need to know about Williamstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Williamstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Williamstown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Williamstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Williamstown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Williamstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Williamstown holiday rentals we have selected for you start as low as NZ$219 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Williamstown rentals

At Expedia, we put the best Williamstown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Williamstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Williamstown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Williamstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox: This highly rated holiday home rental in Williamstown is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Williamstown?

Choose from 35 Expedia holiday rentals in Williamstown for a memorable holiday.

What can I see and do in Williamstown?

Cultural attractions include Williams College Museum of Art and Sterling and Francine Clark Art Institute, 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 Williamstown Theatre Festival 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.