Glendale Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Glendale vacation rentals

House (3 Bedrooms) | 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 ￥30,999
￥87,562 total
includes taxes & fees
Mar 14 - Mar 15
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior detail

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ￥31,458
￥51,391 total
includes taxes & fees
Mar 19 - Mar 20
3-bedroom house in beautiful Berkshires, close to amenities!
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 ￥63,264
￥107,588 total
includes taxes & fees
Mar 15 - Mar 16
Guesthouse Cabin vacation rentals in Berkshire County
Smart TV, books

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires Cottage! Dog 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 ￥25,337
￥60,630 total
includes taxes & fees
Mar 13 - Mar 14
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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 ￥23,724
￥30,114 total
includes taxes & fees
Mar 14 - Mar 15
The Brooks Motel: Exceptional Suite
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 ￥39,856
￥84,623 total
includes taxes & fees
Apr 1 - Apr 2
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 ￥26,191
￥43,566 total
includes taxes & fees
Mar 15 - Mar 16
Home in Great Barrington
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, (34 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 ￥35,467
￥87,317 total
includes taxes & fees
Mar 15 - Mar 16
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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 ￥42,561
￥78,281 total
includes taxes & fees
Mar 13 - Mar 14
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 ￥25,514
￥80,830 total
includes taxes & fees
Mar 17 - Mar 18
Artists’ Hideaway in Old Chatham
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥32,027
￥50,084 total
includes taxes & fees
Mar 15 - Mar 16
Family Ski Getaway in the Berkshires
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 ￥19,762
￥40,290 total
includes taxes & fees
Mar 17 - Mar 18
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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 ￥22,775
￥60,582 total
includes taxes & fees
Mar 16 - Mar 17
Near Tanglewood: Historic Summer Retreat
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 ￥23,512
￥49,745 total
includes taxes & fees
Mar 15 - Mar 16
Charming 3-bedroom Cabin for nature lovers
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 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 ￥28,469
￥72,433 total
includes taxes & fees
Mar 15 - Mar 16
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 ￥31,632
￥52,977 total
includes taxes & fees
Mar 30 - Mar 31
Sugar Shack - 300 square feet of pure sweetness.
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 ￥35,625
￥77,110 total
includes taxes & fees
Mar 15 - Mar 16
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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 ￥37,958
￥48,691 total
includes taxes & fees
Mar 15 - Mar 16
BLUSH: Boutique TINY home*private spa*walk to town
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 ￥37,484
￥79,676 total
includes taxes & fees
Mar 29 - Mar 30
Cheerful 3-bedroom cottage with woodstove
TV

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 ￥41,754
￥88,269 total
includes taxes & fees
Mar 16 - Mar 17
Treetop Hideaway in Tyringham
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Nice place to stay. Beautiful pond and lovely continental breakfast "
Paula 1-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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:

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

Frequently asked questions

Are there vacation rentals in Glendale?

Yes, we offer vacation rentals near the most popular sights in Glendale, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Glendale?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This vacation home near Glendale is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Glendale?

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

What can I see and do in Glendale?

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

What are vacation rentals like in Glendale?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Glendale. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.