Holiday Homes in Glendale

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Glendale holiday homes

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 NZ$671
includes taxes & fees
6 Apr - 7 Apr
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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 NZ$635
includes taxes & fees
6 Apr - 7 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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 NZ$538
includes taxes & fees
2 Apr - 3 Apr
Cozy Riverside Berkshires Retreat

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 NZ$708
includes taxes & fees
5 Apr - 6 Apr
Near Tanglewood: Historic Summer Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 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 NZ$556
includes taxes & fees
13 Apr - 14 Apr
Home in Great Barrington

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 NZ$842
includes taxes & fees
3 Apr - 4 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is NZ$874
includes taxes & fees
2 Apr - 3 Apr
Artists’ Hideaway in Old Chatham

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)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
The price is NZ$1,231
includes taxes & fees
3 Apr - 4 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 NZ$859
includes taxes & fees
6 Apr - 7 Apr
Cheerful 3-bedroom cottage with woodstove

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

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
The price is NZ$561
includes taxes & fees
2 Apr - 3 Apr
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

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 NZ$665
includes taxes & fees
5 Apr - 6 Apr
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 NZ$2,244
includes taxes & fees
2 Apr - 3 Apr
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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 NZ$1,216
includes taxes & fees
2 Apr - 3 Apr
Luxury Barn Retreat — All-Season Escape Awaits!

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 NZ$790
includes taxes & fees
2 Apr - 3 Apr
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
9.0 out of 10, Wonderful, (2 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is NZ$957
includes taxes & fees
2 Apr - 3 Apr
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 NZ$1,339
includes taxes & fees
8 Apr - 9 Apr
Spacious 5-bedroom house in charming Lee with WiFi

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

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
8.0 out of 10, Very good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is NZ$538
includes taxes & fees
2 Apr - 3 Apr
Renovated house. Built in 1890s. No neighbors in sight.

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 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 NZ$955
includes taxes & fees
22 Apr - 23 Apr
Treetop Hideaway in Tyringham

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 NZ$887
includes taxes & fees
13 Apr - 14 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Glendale Hotel Reviews

Find out more about Glendale

Glendale Holiday Homes information

Number of reviews
211
Accommodation
393 Holiday Homes
Lowest Price
NZ$538
Highest Price
NZ$2,244