Glendale Holiday Rentals

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Holiday Rentals in Glendale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (32)
"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.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
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 AU$532
includes taxes & fees
22 Oct - 23 Oct
Sugar Shack - 300 square feet of pure sweetness.
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
United States
Nicole L.
The price is AU$628
includes taxes & fees
21 Oct - 22 Oct
The Blue Elm - A Historic Berkshire Cottage
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is AU$457
includes taxes & fees
21 Oct - 22 Oct
Charming 3-bedroom Cabin for nature lovers
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"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 AU$612
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AU$312
includes taxes & fees
21 Oct - 22 Oct
The Brooks Motel: Exceptional Suite
2 Bed Berkshire Getaway @ Stephentown Hotel
10.0 out of 10, Exceptional, (4)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is AU$425
includes taxes & fees
22 Oct - 23 Oct
2 Bed Berkshire Getaway @ Stephentown Hotel
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AU$398
includes taxes & fees
10 Nov - 11 Nov
Home in Great Barrington
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is AU$1,112
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
Near Tanglewood: Historic Summer Retreat
Berkshires Apartment at the Stephentown Hotel
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 AU$342
includes taxes & fees
21 Oct - 22 Oct
Berkshires Apartment at the Stephentown Hotel
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$753
includes taxes & fees
22 Oct - 23 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
8.4 out of 10, Very good, (12)
"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."
United States
William G.
The price is AU$419
includes taxes & fees
26 Oct - 27 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"No stone left unturned. The hot tub was clean and perfectly situated. the house was clean, with very sweet finishing touches. Within walking distance to shops. Hosts were very responsive. I highly recommend."
United States
Jamie F.
The price is AU$638
includes taxes & fees
27 Oct - 28 Oct
HunnyHAUS: Deluxe TINY*private spa*walk to town
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AU$652
includes taxes & fees
21 Oct - 22 Oct
Bungalow in the Berkshires
Artists’ Hideaway in Old Chatham
The price is AU$688
includes taxes & fees
21 Oct - 22 Oct
Artists’ Hideaway in Old Chatham
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AU$1,192
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$621
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$704
includes taxes & fees
9 Nov - 10 Nov
Cheerful 3-bedroom cottage with woodstove
Berkshire House Stay
9.8 out of 10, Exceptional, (19)
"Incredible location and immaculate home created such a great long weekend for our family. The house has everything you’ll need, organized and spotless. The owner was on top of every detail and communicated immediately. "
United Kingdom
Michael F.
Berkshire House Stay
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

Find out more about Glendale

Everything you need to know about Glendale holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Glendale holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Glendale holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Glendale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Glendale. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Glendale holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Glendale holiday rentals we have selected for you start as low as AU$402 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Glendale rentals

At Expedia, we put the best Glendale holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Glendale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Glendale holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Glendale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water": This holiday home rental outside of Glendale is located on a river, and offers a fireplace, laundry facilities and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

How many holiday rentals are there in Glendale?

Choose from 5 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.