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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 40 Cottages in Williamsburg with updated reviews, rates, and availability.

The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Paper towels

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Picturesque Cottage with Sunroom on Ashmere Lake!
Interior

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
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
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
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
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (2 Bedrooms) | 2 bedrooms, iron/ironing board, bed sheets

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Historic Huntington Home - Walk to Westfield River
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Picturesque Cottage With Sunroom on Ashmere Lake!
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!
TV, fireplace

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

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Entire cottage in Berkshire Villiage

Entire cottage in Berkshire Villiage

3.0 star property
9.4 out of 10, Exceptional, (3)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Becket Home w/ 3-season Porch: Walk to Lake Access
Interior

Becket Home w/ 3-season Porch: Walk to Lake Access

3.0 star property
Becket Home w/ 3-season Porch: Walk to Lake Access
Cozy Southern Vermont Home w/ On-site Trails
Exterior

Cozy Southern Vermont Home w/ On-site Trails

3.0 star property
Cozy Southern Vermont Home w/ On-site Trails
Black Bear Mountain Cottage
Aerial view

Black Bear Mountain Cottage

Black Bear Mountain Cottage
Lakefront Summer Cottage~Sparkling clean social distancing space

Lakefront Summer Cottage~Sparkling clean social distancing space

10.0 out of 10, Exceptional, (1)
"The hosts are lovely. The lake is clean and inviting--perfect for swimming, canoeing, kayaking, sailing, etc.. Beautiful lawn with shade and sun to relax and enjoy the view. Gorgeous flowers everywhere. Elevation helps beat the heat of the valley, keeping temps comfortable with nice breeze off lake. Fun little towns to visit. Next door to state forest with trails. Easy drive to Nothhampton. Fresh farm stand around the corner. Cottages are simple, clean and well-stocked. As hosts indicate, there...
Lakefront Summer Cottage~Sparkling clean social distancing space
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Interior

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

3.0 star property
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Entire home in Dalton, Massachusetts, United States
Terrace/patio

Entire home in Dalton, Massachusetts, United States

Entire home in Dalton, Massachusetts, United States
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

3.0 star property
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Interior

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

3.0 star property
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
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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Other property types in Williamsburg

Experience a charming 3 bedroom farm stay close to winter activity.
Exterior

Experience a charming 3 bedroom farm stay close to winter activity.

10.0 out of 10, Exceptional, (27)
"Old house with new amenities - love the charm of this western MA home. Our family of five stayed here for a nearby wedding and it was effortless including checkout! Host was very accommodating as well."
The price is AED 932
AED 1,416 total
includes taxes & fees
5 May - 6 May
Experience a charming 3 bedroom farm stay close to winter activity.
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.