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Dec 19 - Dec 21
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Jan 9 - Jan 11
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Our top choices for Washington vacation homes

Interior
Home in the Woods

Home in the Woods

Home in the Woods
Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
Home in the Woods
Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Dec 15 - Dec 16
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$349 nightly
The price is $390
Dec 15 - Dec 16
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$207 nightly
The price is $231
Dec 15 - Dec 16
Total with taxes and fees
Home in Great Barrington
Interior
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
$332 nightly
The price is $372
Dec 14 - Dec 15
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
$339 nightly
The price is $358
Dec 15 - Dec 16
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$455 nightly
The price is $510
Dec 14 - Dec 15
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Outdoor dining
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$434 nightly
The price is $485
Dec 15 - Dec 16
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$398 nightly
The price is $445
Dec 14 - Dec 15
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Interior
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$217 nightly
The price is $242
Dec 15 - Dec 16
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 15 - Dec 16
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Smart TV, DVD player, books, stereo
Great Barrington Get Away

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$461 nightly
The price is $515
Dec 14 - Dec 15
Total with taxes and fees
Great Barrington Get Away
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
$722 nightly
The price is $733
Dec 14 - Dec 15
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
TV, fireplace, printers
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (2)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
$1,189 nightly
The price is $1,328
Dec 15 - Dec 16
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Pool
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
$487 nightly
The price is $544
Dec 14 - Dec 15
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Outdoor dining
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,015 nightly
The price is $1,099
Dec 15 - Dec 16
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Exterior detail
3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
$379 nightly
The price is $423
Jan 12 - Jan 13, 2026
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!
Fridge, microwave, oven, stovetop
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.0 out of 10, Very Good, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
$743 nightly
The price is $830
Dec 21 - Dec 22
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop
Berkshire House Stay

Berkshire House Stay

Berkshire House Stay
Lee
10.0 out of 10, Exceptional, (21)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
Berkshire House Stay
Interior
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
$418 nightly
The price is $468
Dec 19 - Dec 20
Total with taxes and fees
Artists’ Hideaway in Old Chatham
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 Washington Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Washington

Washington Vacation Homes information

Number of reviews
398
Accommodation
371 Vacation Homes
Lowest Price
$231
Highest Price
$1,328

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