Glendale Holiday Homes
Massachusetts
United States of America
Holiday Homes
Expedia.ie

Hotels in Glendale Holiday Rentals in Glendale Glendale Car Hire Glendale Holiday Packages

Holiday Homes in Glendale

Where to?

Dates

Wed, 28 Jan

Thu, 29 Jan

your current months are January, 2026 and February, 2026.

January 2026

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

SunSunday

February 2026

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

SunSunday

Travellers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Glendale holiday homes

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

Sherwood Forest

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

Sharon K.

The price is €331

€331

includes taxes & fees

21 Jan - 22 Jan

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

2 bedrooms, desk, iron/ironing board, travel cot

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

Sherwood Forest

9.6 out of 10, Exceptional, (10 reviews)

9.6/10

Exceptional

(10 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."

James D.

The price is €338

€338

includes taxes & fees

21 Jan - 22 Jan

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

Home in Great Barrington

Great Barrington

9.8 out of 10, Exceptional, (26 reviews)

9.8/10

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. "

Cameron M.

The price is €220

€220

includes taxes & fees

26 Jan - 27 Jan

Home in Great Barrington

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Near Tanglewood: Historic Summer Retreat

New Lebanon

9.2 out of 10, Wonderful, (25 reviews)

9.2/10

Wonderful

(25 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

Paul S.

The price is €317

€317

includes taxes & fees

25 Jan - 26 Jan

Near Tanglewood: Historic Summer Retreat

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

2.0 star property

Stephentown

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"excellent communication with property manager."

Nancy H.

The price is €488

€488

includes taxes & fees

15 Jan - 16 Jan

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

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 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."

Sarah D.

The price is €406

€406

includes taxes & fees

19 Jan - 20 Jan

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

10.0 out of 10, Exceptional, (3 reviews)

10/10

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."

Cheryl F.

The price is €214

€214

includes taxes & fees

1 Feb - 2 Feb

Sweet Cozy Victorian in Housatonic. Close to everything.

3 bedrooms, desk, iron/ironing board, WiFi

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

2.0 star property

Pittsfield

7.8 out of 10, Good, (7 reviews)

7.8/10

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."

Liz V.

The price is €435

€435

includes taxes & fees

16 Jan - 17 Jan

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

Smart TV, fireplace, books, music library

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs

8.8 out of 10, Excellent, (20 reviews)

8.8/10

Excellent

(20 reviews)

"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "

Wendy D.

The price is €328

€328

includes taxes & fees

15 Jan - 16 Jan

Historic Berkshires Home Near Tanglewood, Trails & Wineries

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

Stockbridge

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 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. "

cathy c.

The price is €573

€573

includes taxes & fees

19 Jan - 20 Jan

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

Microwave, oven, stovetop, eco-friendly cleaning products

Family Ski Getaway in the Berkshires

Great Barrington

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

Cristine C.

The price is €262

€262

includes taxes & fees

26 Jan - 27 Jan

Family Ski Getaway in the Berkshires

Suite 3 - Quiet and private accommodations in a country setting.

Spencertown

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Fantastic place to stay!"

James

The price is €241

€241

includes taxes & fees

25 Jan - 26 Jan

Suite 3 - Quiet and private accommodations in a country setting.

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Monterey

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."

Kim H.

The price is €1,518

€1,518

includes taxes & fees

18 Jan - 19 Jan

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

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

2.0 star property

Chatham

The price is €267

€267

includes taxes & fees

25 Jan - 26 Jan

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

Great Barrington Get Away

Great Barrington

9.4 out of 10, Exceptional, (26 reviews)

9.4/10

Exceptional

(26 reviews)

"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!"

Elizabeth G.

The price is €486

€486

includes taxes & fees

15 Jan - 16 Jan

Great Barrington Get Away

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is €1,013

€1,013

includes taxes & fees

21 Jan - 22 Jan

Hancock Village Inn Near Jiminy Peak

Catamount, Zip Line, Private Setting, Book Now!

Egremont

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."

Jason W.

The price is €1,017

€1,017

includes taxes & fees

19 Jan - 20 Jan

Catamount, Zip Line, Private Setting, Book Now!

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

Great Barrington

10.0 out of 10, Exceptional, (3 reviews)

10/10

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!"

Roberta

The price is €1,170

€1,170

includes taxes & fees

15 Jan - 16 Jan

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

Artists’ Hideaway in Old Chatham

Old Chatham

The price is €486

€486

includes taxes & fees

15 Jan - 16 Jan

Artists’ Hideaway in Old Chatham

Smart TV, fireplace, video games, ping pong

5 bedrooms, desk, iron/ironing board, WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee

8.8 out of 10, Excellent, (3 reviews)

8.8/10

Excellent

(3 reviews)

"House was clean and made our Thanksgiving great with it's size and amenities. "

Khalil S.

Spacious 5-bedroom house in charming Lee with WiFi

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.

View all properties