Glendale Holiday Rentals

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Check prices for these dates

Tonight
1 Jan - 2 Jan
Tomorrow
2 Jan - 3 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Glendale holiday rentals

Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$957
HK$1,847 total
includes taxes & fees
5 Jan - 6 Jan
Berkshires Apartment at the Stephentown Hotel
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is HK$1,051
HK$1,607 total
includes taxes & fees
3 Jan - 4 Jan
Charming Apt in 18th c Berkshire Farmhouse
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

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

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,135
HK$2,911 total
includes taxes & fees
5 Jan - 6 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
7.0 out of 10, Good, (2)
"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$1,206
HK$2,488 total
includes taxes & fees
3 Jan - 4 Jan
Charming 3-bedroom Cabin for nature lovers
Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

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$1,525
HK$4,308 total
includes taxes & fees
6 Jan - 7 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,394
HK$3,426 total
includes taxes & fees
5 Jan - 6 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"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. "
United States
Cameron M.
The price is HK$1,177
HK$2,001 total
includes taxes & fees
6 Jan - 7 Jan
Home in Great Barrington
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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."
United States
James D.
The price is HK$1,247
HK$3,052 total
includes taxes & fees
4 Jan - 5 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is HK$1,051
HK$2,894 total
includes taxes & fees
6 Jan - 7 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3)
"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."
United States
Sarah D.
The price is HK$1,401
HK$3,572 total
includes taxes & fees
7 Jan - 8 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4)
"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$1,237
HK$1,569 total
includes taxes & fees
11 Jan - 12 Jan
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (23)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$1,331
HK$3,251 total
includes taxes & fees
5 Jan - 6 Jan
Near Tanglewood: Historic Summer Retreat
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

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, (6)
"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$1,557
HK$2,659 total
includes taxes & fees
6 Jan - 7 Jan
BLUSH: Boutique TINY home*private spa*walk to town
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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
2.0 star property
Stephentown
The price is HK$1,362
HK$4,385 total
includes taxes & fees
6 Jan - 7 Jan
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Games room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
United States
Kathy C.
The price is HK$1,576
HK$2,316 total
includes taxes & fees
13 Jan - 14 Jan
Family Ski Getaway in the Berkshires
Exterior
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
The price is HK$6,942
HK$13,450 total
includes taxes & fees
12 Jan - 13 Jan
Berkshires farm, 30+ guests, 50 acres
Property grounds
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"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$1,673
HK$2,808 total
includes taxes & fees
12 Jan - 13 Jan
Sugar Shack - 300 square feet of pure sweetness.
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9)
"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$3,058
HK$5,397 total
includes taxes & fees
5 Jan - 6 Jan
Guesthouse Cabin vacation rentals in Berkshire County
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is HK$1,751
HK$3,212 total
includes taxes & fees
13 Jan - 14 Jan
HunnyHAUS: Deluxe TINY*private spa*walk to town
Property grounds
3-bedroom house in beautiful Berkshires, close to amenities!

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,450
HK$2,445 total
includes taxes & fees
12 Jan - 13 Jan
3-bedroom house in beautiful Berkshires, close to amenities!
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 Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"The room was spotless, staff was friendly, and the facility was extremely clean. If in the area we will definately stay here again."
Michelle 1-night trip
Posted 3 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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.