Williamstown holiday homes

We found 275 holiday rentals — enter your dates for availability
Discover a selection of 36 homes and other holiday rentals in Williamstown that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Williamstown

Showing deals for:18 Dec - 25 Dec

Living area
Private kitchen
Interior
Interior
Exceptional
(7 reviews)

Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY

Cropseyville

8% off
NZ$20,550
for 7 nights, 1 home
NZ$2,936 per night
includes taxes & fees
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
Build a cozy fire in our wood fireplace, watch the game or play pool!
Beautiful period woodwork and Victorian details
Walk to Spring Street and brand new Williams Bookstore
Gourmet kitchen has everything you need to prepare delicious meals
Exceptional
(157 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
NZ$10,304
for 7 nights, 1 home
NZ$1,472 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Living area
Terrace/patio
Private kitchen
Room
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,103
for 7 nights, 1 cottage
NZ$729 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Property grounds
Outdoor dining
Dining
Renovated kitchen
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,713
for 7 nights, 1 home
NZ$959 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Living area
Interior
Interior
Exterior
Exceptional
(41 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
NZ$2,920
for 7 nights, 1 home
NZ$417 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Views from the back of the 16 acres on the property
View from 2nd floor balcony (after leaves have fallen)
Smart TV in Downstairs room with view of entrance to house and doors to room
Entrance into house with wood burning stove to right and staircase
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$4,208
for 7 nights, 1 home
NZ$601 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Interior
Spring at Jiminy Peak 2019
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

13% off
NZ$15,486
for 7 nights, 1 home
NZ$2,212 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Interior
Private kitchen
Private kitchen
Room
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$4,647
for 7 nights, 1 home
NZ$664 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Room
Owner and guest parking. Private guest access is located through the porch door.
Exterior detail
Hallway view from the bathroom looking toward the kitchen area.
Exceptional
(34 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
NZ$1,688
for 7 nights, 1 apartment
NZ$241 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
another view of same bedroom as well as makeup table
new backyard table
Beaver Pond Pool/clubhouse
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,253
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Interior
Interior
Room
Bathroom
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,786
for 7 nights, 1 home
NZ$684 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Bow Window in Master Bedroom Overlooking Main Street
Rear Entry Staircase & Sun Room
Living area
Exterior detail
Exceptional
(11 reviews)

Luxury Living High Above the Center of Town.

Bennington

8% off
NZ$3,734
for 7 nights, 1 apartment
NZ$533 per night
includes taxes & fees
Luxury Living High Above the Center of Town.
Interior
Living area
Living area
Interior
Very good
(5 reviews)

Walk to campus; open concept kitchen/living;nature trail at end of this quiet st

Williamstown

14% off
NZ$3,545
for 7 nights, 1 home
NZ$506 per night
includes taxes & fees
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Interior
Exterior
Exterior detail
Front covered porch for people watching and catching summer breezes.
Exceptional
(7 reviews)

Downtown Victorian House

Bennington

12% off
NZ$2,918
for 7 nights, 1 apartment
NZ$417 per night
includes taxes & fees
Downtown Victorian House

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The arty area of Williamstown awaits your stay

Take a holiday to Williamstown and enjoy the area's art galleries, museums and theatre scene. This scenic city is known for its university setting, hiking and skiing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Williamstown

Are you hoping to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Williamstown has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Waubeeka Golf Links (4.2 mi / 6.8 km)
  • Jiminy Peak Mountain Resort (11.7 mi / 18.9 km)
  • Prospect Mountain Cross-Country Ski Center (13.1 mi / 21.1 km)
  • Berkshire East Ski Resort (18 mi / 29 km)
  • Bousquet Ski Area (20.9 mi / 33.6 km)
  • Wyndhurst Golf & Club (25.7 mi / 41.3 km)

Exploring the natural features in Williamstown

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Williamstown is a great spot to appreciate mother nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Mount Greylock State Reservation (5 mi / 8 km)
  • Mount Greylock (5.5 mi / 8.8 km)
  • Brodie Mountain (5.7 mi / 9.1 km)
  • Taconic Lake (10.7 mi / 17.3 km)
  • Mount Greylock State Reservation Visitor Center (10.9 mi / 17.6 km)
  • Grafton Lakes State Park (13.3 mi / 21.4 km)

Transport to and around Williamstown

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 20.3 mi (32.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Albany, NY (ALB-Albany Intl.), which is 30.8 mi (49.6 km) away.

Frequently asked questions

What is the best area to stay in Williamstown when booking a holiday rental?
When considering the best area to stay in Williamstown, Massachusetts, a fantastic choice would be the vicinity around the Williams College campus. This area not only offers a range of holiday rental properties but also immerses you in the vibrant academic atmosphere of the college. You can enjoy easy access to the Williams College Museum of Art, which boasts an impressive collection of American art, and the stunning natural beauty of the surrounding Berkshires.Another appealing option is the area near the quaint downtown, where you'll find charming shops and delightful eateries. Staying here allows you to explore the local culture and perhaps catch a performance at the renowned Williamstown Theatre Festival.
Where are the best Williamstown ski resort rentals?
For the best ski resort rentals near Williamstown, Massachusetts, travellers should focus on the nearby Mount Greylock area, which offers excellent access to outdoor winter activities. The quaint town of Williamstown itself features a selection of charming rental properties, including cosy cabins and spacious homes, all within a short drive to the slopes. Many accommodations are equipped with essential amenities such as fully stocked kitchens, fireplaces, and comfortable living areas, ideal for unwinding after a day of skiing.In addition, properties in Williamstown often provide access to local attractions, such as the Williams College Museum of Art and the scenic surroundings of the Berkshires. Visitors can also find rentals that boast outdoor spaces, like decks or patios, which are superb for enjoying the winter landscape. For those seeking a more rustic experience, nearby towns like New Ashford and Lanesborough offer a range of traditional New England homes, some of which include features like wood-burning stoves and access to hiking trails, allowing for an extensive winter getaway.
What is the most popular type of holiday rental accomodation in Williamstown?
In Williamstown, holiday houses are the most popular type of holiday rental, with around 132 available across the picturesque town. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and outdoor areas ideal for relaxation after a day of exploring the local attractions, such as the Williams College Museum of Art and the beautiful landscapes of the Berkshires. Additionally, there are about 36 apartments and 24 condos that provide a more compact yet comfortable stay, generally equipped with modern amenities and convenient access to local dining and shopping options. For those seeking a quaint escape, around 20 cottages are available, offering a charming, rustic atmosphere.
Are there any family house rentals in Williamstown?
In Williamstown, Massachusetts, there are many family-friendly house rentals available, with around 41 options to choose from. This charming town, known for its picturesque landscapes and vibrant arts scene, offers a variety of properties suited for families. Many homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can enjoy fresh air and play.Visitors will appreciate the proximity to local attractions, such as the Williams College Museum of Art and the scenic Mount Greylock State Reservation, which is superb for hiking and outdoor activities. Additionally, several rental properties include amenities like Wi-Fi, air conditioning, and even game rooms, ensuring a comfortable and entertaining stay for all ages.
Can I rent a holiday home with a pool or hot tub in Williamstown?
In Williamstown, there are several holiday homes available for rent that feature pools, with around 11 options to choose from. This picturesque town, located in the Berkshires, offers a serene environment ideal for relaxation and outdoor activities. Many of these properties come with amenities such as private pools, hot tubs, and spacious outdoor areas great for family gatherings or quiet evenings under the stars.Travellers can also expect fully equipped kitchens, comfortable living spaces, and sometimes even scenic views of the surrounding mountains. The area is rich in cultural attractions, including the renowned Clark Art Institute, making it a great destination for those looking to combine relaxation with exploration.
Are there pet-friendly house rentals in Williamstown?
In Williamstown, there are several pet-friendly house rentals available, with around 15 options for travellers seeking to bring their furry companions along. Many of these properties offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them suitable for families or groups.The town is surrounded by stunning natural beauty, including the nearby Mount Greylock State Reservation, which provides ample opportunities for outdoor adventures with pets, such as hiking and exploring scenic trails. Additionally, the charming downtown area features pet-friendly cafes and shops, ideal for those travelling with their dogs.
Are there any remote work holiday rentals in Williamstown?
In Williamstown, Massachusetts, there are numerous options for remote work holiday rentals, with around 204 available throughout the area. This charming town, known for its picturesque landscapes and cultural attractions, provides a conducive environment for remote workers. Many properties feature essential amenities such as reliable Wi-Fi, dedicated workspaces, and comfortable living areas to ensure a productive stay. Additionally, some rentals may offer more specialized features like safe in-room options and access to third-party internet services, catering specifically to those who need to stay connected.The town is home to top sites like Williams College and the Clark Art Institute, which can provide a delightful break from work. The surrounding natural beauty allows for leisurely walks or hikes in the nearby mountains, making it a great blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Williamstown?
In Williamstown, holiday rentals typically feature a range of amenities that cater to the needs of travellers. Most properties come equipped with a kitchen, allowing guests to prepare their own meals, while many also include a deck or patio, providing a lovely outdoor space to relax and enjoy the fresh air. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, many rentals offer coffee and tea-making facilities, as well as blenders for those who appreciate a morning smoothie or a quick snack.
When is the best time to visit Williamstown for a holiday rental?
The peak season for visiting Williamstown is during the summer months, specifically from June to August, with July being the most popular time for holiday rentals. This period attracts a diverse crowd, including art enthusiasts who flock to the renowned Massachusetts Museum of Contemporary Art and nature lovers who revel in the region's picturesque landscapes.During these warm months, temperatures typically hover between 20 to 30 degrees Celsius, creating an inclusive setting for outdoor activities such as hiking the scenic trails of Mount Greylock or enjoying a leisurely stroll through the charming town centre. With vibrant festivals and events, July offers a lively option that enhances the experience of exploring this cultural gem.For those looking for a more budget-friendly option, visiting Williamstown in December can be a delightful choice. While it falls outside the peak season, this month offers a unique charm with quiet streets, festive decorations, and opportunities for winter activities like snowshoeing and cross-country skiing.
What are the top attractions in Williamstown?
In Williamstown, visitors can take part in a variety of attractions that highlight the town's rich cultural and natural heritage. The Clark Art Institute is a major draw, featuring an impressive collection of European and American art, surrounded by beautiful landscapes and walking trails. Nearby, Williams College offers picturesque campus grounds, and the Williams College Museum of Art showcases contemporary and historic works.For those who enjoy the outdoors, Mount Greylock State Reservation is just a short drive away, providing stunning vistas and hiking opportunities, including the challenging hike to the summit of Mount Greylock, the highest peak in Massachusetts. The Sterling and Francine Clark Art Institute's gardens also offer a serene setting for a leisurely stroll.Additionally, the town hosts various cultural events and festivals throughout the year, enriching the experience for both residents and visitors.
Are all fees included in the Williamstown holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Williamstown holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Williamstown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Williamstown holiday homes?
You can find great discounts on holiday homes in Williamstown on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Williamstown holiday home booking on Bookabach?
To find Williamstown holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Williamstown?
A long-stay holiday home in Williamstown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Williamstown holiday home?
Book your Williamstown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Williamstown?
Prices for holiday homes in Williamstown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Williamstown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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