Glendale Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Glendale holiday rentals

Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,531
HK$3,636 total
includes taxes & fees
8 Apr - 9 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 HK$1,256
HK$3,083 total
includes taxes & fees
7 Apr - 8 Apr
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 HK$1,143
HK$2,940 total
includes taxes & fees
8 Apr - 9 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls Home w/ Fire Pit: Hike & Ski!
3.0 star property
Ashley Falls
9.6 out of 10, Exceptional, (4 reviews)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
United States
JAY
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,135
HK$5,358 total
includes taxes & fees
8 Apr - 9 Apr
Guesthouse Cabin vacation rentals in Berkshire County
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,176
HK$1,492 total
includes taxes & fees
5 Apr - 6 Apr
The Brooks Motel: Exceptional Suite
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 HK$1,587
HK$2,482 total
includes taxes & fees
6 Apr - 7 Apr
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 HK$1,340
HK$3,274 total
includes taxes & fees
5 Apr - 6 Apr
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

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 HK$1,608
HK$2,488 total
includes taxes & fees
16 Apr - 17 Apr
Home in Great Barrington
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is HK$1,004
HK$2,031 total
includes taxes & fees
8 Apr - 9 Apr
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$2,038
HK$2,590 total
includes taxes & fees
9 Apr - 10 Apr
BLUSH: Boutique TINY home*private spa*walk to town
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is HK$1,764
HK$2,890 total
includes taxes & fees
9 Apr - 10 Apr
Sugar Shack - 300 square feet of pure sweetness.
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 HK$2,109
HK$3,879 total
includes taxes & fees
4 Apr - 5 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

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

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,536
HK$4,339 total
includes taxes & fees
5 Apr - 6 Apr
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is HK$1,264
HK$3,971 total
includes taxes & fees
14 Apr - 15 Apr
Artists’ Hideaway in Old Chatham
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)
"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 HK$2,814
HK$5,690 total
includes taxes & fees
4 May - 5 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
6.8 out of 10, (3 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is HK$1,033
HK$2,295 total
includes taxes & fees
4 Apr - 5 Apr
Charming 3-bedroom Cabin for nature lovers
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 HK$1,858
HK$3,957 total
includes taxes & fees
6 Apr - 7 Apr
Cheerful 3-bedroom cottage with woodstove
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 HK$1,756
HK$3,802 total
includes taxes & fees
5 Apr - 6 Apr
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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 HK$1,453
HK$3,628 total
includes taxes & fees
5 Apr - 6 Apr
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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

Hotel On North

Hotel On North

10/10 Excellent
"What a lovely room and building. Really enjoyed this hotel. However, the neighborhood outside the hotel was very sketchy and clearly there is an issue with drug addiction in the area. I ate at the restaurant within the hotel and went to and from my car in the gated lot. I enjoyed many other towns in the Berkshires, but Pittsfield was not one of them. Wish this hotel was in a different city, as I would love to stay there again. "
Susan 3-night trip
Posted 2 hours ago
Hotel On North

Find out more about Glendale

Search for holiday rentals in Glendale on Expedia! You can easily find your home rentals, villas, holiday apartments in Glendale using one of the methods below:

  • View our selection of featured holiday rentals in Glendale
  • Use the map to find apartments and other holiday homes in the Glendale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Glendale while they last

Look no further and take a look at our great range of rental properties in Glendale!

Frequently asked questions

Are there holiday rentals in Glendale?

Yes, there are holiday rentals close to the most popular sights in Glendale, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Glendale has to offer?

Peace and quiet on the lake: This holiday home rental outside of Glendale is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Glendale?

Choose from 6 Expedia holiday rentals in Glendale for a memorable holiday.

What can I see and do in Glendale?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Housatonic River. In the wider area, you’ll find Norman Rockwell Museum and Naumkeag Museum.

What are holiday rentals like in Glendale?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Glendale. Holiday rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.