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Cottages in Williamstown

Our top choices for Williamstown cottages

Near Hiking & Skiing: Home in Wilmington!
House (3 Bedrooms) | Interior

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!
Charlemont Retreat on Chickley River w/ EV Charger
Interior

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Bennington Gem w/ Smart TV Near Historic District!
House (1 Bedroom) | Interior

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!
Wilmington Vacation Rental Near Hiking and Skiing!
Dining

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
Luxury Vacation Rental in the Berkshires!
House (3 Bedrooms) | Interior

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Cozy Wilmington Home: 6 Mi to Mount Snow!
House (4 Bedrooms) | Interior

Cozy Wilmington Home: 6 Mi to Mount Snow!

3.0 star property
Cozy Wilmington Home: 6 Mi to Mount Snow!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
House (1 Bedroom) | Interior

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
'john's Farmhouse in Mount Snow' on 120 Acres!
House (5 Bedrooms) | Interior

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
House (4 Bedrooms) | Interior

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Expansive Upstate Home w/ Home Theater!
House (5 Bedrooms) | Interior

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
House (2 Bedrooms) | Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Berkshire Hideaway w/ Fire Pit & Playground!
House (3 Bedrooms) | Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Stockbridge Home: Walk to Town Beach!
House (3 Bedrooms) | Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Picturesque Cottage With Sunroom on Ashmere Lake!
Cottage (3 Bedrooms) | Interior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
House (5 Bedrooms) | Interior

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
2 Mi to Hoosic River: 'the Moss House' w/ Deck!
House (3 Bedrooms) | Interior

2 Mi to Hoosic River: 'the Moss House' w/ Deck!

3.0 star property
2 Mi to Hoosic River: 'the Moss House' w/ Deck!
Massachusetts Vacation Rental w/ Deck & Grill
4 bedrooms, desk, laptop workspace, bed sheets

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
12-acre Vacation Rental in the Berkshires!
Property grounds

12-acre Vacation Rental in the Berkshires!

3.0 star property
12-acre Vacation Rental in the Berkshires!
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

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Great stay. Well balanced, clean, friendly. "
Derek 1-night trip
Posted 1 day ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

Why book your cottage in Williamstown with Expedia?
Expedia has some great cottages in Williamstown, so start packing for a memorable vacation close to nature. If you have a budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make the most of our filters to search for cottages with free WiFi or a pool. We'll help you find the right place whatever your plans or bank balance.
How can I find cheap cottages in Williamstown?
With Expedia's convenient filter tool, comparing cheap cottages in Williamstown has never been simpler. To find accommodations that'll make your bank balance smile, tailor your search results by amenities, budget and star rating.
What is there to do in Williamstown near my cottage?
Whatever you're interested in, Williamstown has loads to keep you entertained. Chapin Library of Rare Books and Manuscripts, Hopkins Observatory and Williams College Museum of Art are on many travelers' to-do lists. Don't miss The Clark Art Institute, Williamstown Theatre Festival and Sterling and Francine Clark Art Institute either. With Expedia's hotel deals in Williamstown, you'll be able to see more renowned attractions like these with the cash you save.