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Our top choices for Glendale vacation homes

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
9.8 out of 10, Exceptional, (11 reviews)
"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.
The price is ¥24,796
¥61,064 total
includes taxes & fees
Feb 3 - Feb 4
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ¥21,669
¥57,727 total
includes taxes & fees
Feb 24 - Feb 25
Near Tanglewood: Historic Summer Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ¥26,777
¥44,086 total
includes taxes & fees
Feb 23 - Feb 24
Home in Great Barrington

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is ¥20,895
¥41,493 total
includes taxes & fees
Feb 3 - Feb 4
Sweet Cozy Victorian in Housatonic. Close to everything.

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is ¥21,453
¥58,176 total
includes taxes & fees
Feb 3 - Feb 4
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is ¥27,860
¥70,711 total
includes taxes & fees
Feb 8 - Feb 9
Sun Filled Lenox Retreat - Minutes to Tanglewood!

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥27,087
¥85,993 total
includes taxes & fees
Feb 3 - Feb 4
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is ¥44,112
¥80,394 total
includes taxes & fees
Mar 1 - Mar 2
Great Barrington Get Away

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥31,343
¥46,075 total
includes taxes & fees
Feb 3 - Feb 4
Family Ski Getaway in the Berkshires

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is ¥46,279
¥100,621 total
includes taxes & fees
Feb 3 - Feb 4
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ¥52,625
¥90,939 total
includes taxes & fees
Feb 8 - Feb 9
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is ¥51,851
¥97,078 total
includes taxes & fees
Feb 9 - Feb 10
Luxury Barn Retreat — All-Season Escape Awaits!

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ¥29,393
¥49,428 total
includes taxes & fees
Feb 16 - Feb 17
3-bedroom house in beautiful Berkshires, close to amenities!

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!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ¥41,651
¥76,435 total
includes taxes & fees
Feb 3 - Feb 4
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
The price is ¥51,851
¥65,871 total
includes taxes & fees
Feb 3 - Feb 4
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ¥89,223
¥167,554 total
includes taxes & fees
Feb 4 - Feb 5
Hancock Village Inn Near Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ¥73,521
¥133,299 total
includes taxes & fees
Feb 12 - Feb 13
Spacious 5-bedroom house in charming Lee with WiFi

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, (3 reviews)
"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
The price is ¥87,621
¥205,583 total
includes taxes & fees
Feb 4 - Feb 5
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is ¥27,087
¥48,366 total
includes taxes & fees
Feb 3 - Feb 4
Renovated house. Built in 1890s. No neighbors in sight.

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is ¥24,969
¥79,450 total
includes taxes & fees
Feb 3 - Feb 4
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 Glendale Hotel Reviews

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Glendale Vacation Homes information

Number of reviews
11,823
Accommodation
393 Vacation Homes
Lowest Price
¥11,929
Highest Price
¥69,467