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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Glendale vacation homes

Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ￥25,515
￥62,123 total
includes taxes & fees
Apr 15 - Apr 16
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,222
￥59,919 total
includes taxes & fees
Apr 15 - Apr 16
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (29 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is ￥32,272
￥51,180 total
includes taxes & fees
Apr 20 - Apr 21
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (13 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥32,252
￥50,436 total
includes taxes & fees
Apr 22 - Apr 23
Cozy Riverside Berkshires Retreat
Exterior

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 ￥18,635
￥54,764 total
includes taxes & fees
Apr 18 - Apr 19
Near Tanglewood: Historic Summer Retreat
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is ￥35,715
￥76,947 total
includes taxes & fees
Apr 15 - Apr 16
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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!
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 ￥42,860
￥78,653 total
includes taxes & fees
Apr 15 - Apr 16
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is ￥25,693
￥80,684 total
includes taxes & fees
Apr 15 - Apr 16
Artists’ Hideaway in Old Chatham
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,747
￥80,414 total
includes taxes & fees
Apr 20 - Apr 21
Cheerful 3-bedroom cottage with woodstove
Exterior

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, (35 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥57,178
￥115,638 total
includes taxes & fees
Apr 22 - Apr 23
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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
Great Barrington
10.0 out of 10, Exceptional, (4 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 ￥90,593
￥212,205 total
includes taxes & fees
Apr 15 - Apr 16
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥42,047
￥88,888 total
includes taxes & fees
Apr 22 - Apr 23
Treetop Hideaway in Tyringham
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥27,872
￥89,017 total
includes taxes & fees
Apr 15 - Apr 16
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Property grounds

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

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is ￥27,872
￥48,877 total
includes taxes & fees
Apr 15 - Apr 16
Renovated house. Built in 1890s. No neighbors in sight.
3 bedrooms, iron/ironing board, WiFi, bed sheets

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 ￥45,392
￥81,838 total
includes taxes & fees
Apr 15 - Apr 16
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is ￥17,838
￥54,228 total
includes taxes & fees
Apr 15 - Apr 16
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
Fridge, microwave, oven, stovetop

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 ￥75,653
￥137,165 total
includes taxes & fees
Apr 22 - Apr 23
Spacious 5-bedroom house in charming Lee with WiFi
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.8 out of 10, Exceptional, (6 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is ￥50,600
￥100,463 total
includes taxes & fees
Apr 15 - Apr 16
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥100,173
￥182,998 total
includes taxes & fees
May 5 - May 6
Hancock Village Inn Near Jiminy Peak
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The room was comfortable, and clean. The staff was very courteous and helpful. Breakfast was adequate. Check in and check out went smoothly."
Sharon 2-night trip
Posted 3 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Glendale

Glendale Vacation Homes information

Number of reviews
233
Accommodation
393 Vacation Homes
Lowest Price
￥48,877
Highest Price
￥212,205