Glendale Holiday Rentals

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Holiday Rentals in Glendale

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The price is NZ$248
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow

Apartment in Lanesborough

9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
The price is NZ$370
includes taxes & fees
23 Nov - 24 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in 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 NZ$382
includes taxes & fees
23 Nov - 24 Nov
Berkshires Apartment at the Stephentown Hotel

Holiday Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$672
includes taxes & fees
24 Nov - 25 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Cabin in Hinsdale

9.8 out of 10, Exceptional, (33)
"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 NZ$755
includes taxes & fees
24 Nov - 25 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Holiday Home in 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 NZ$699
includes taxes & fees
1 Dec - 2 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Holiday Home in Great Barrington

9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
The price is NZ$485
includes taxes & fees
2 Dec - 3 Dec
Home in Great Barrington

Holiday Home in 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.
Near Tanglewood: Historic Summer Retreat

Cabin in 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 NZ$569
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom Cabin for nature lovers

Holiday Home in Housatonic

10.0 out of 10, Exceptional, (3)
"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."
United States
Cheryl F.
The price is NZ$432
includes taxes & fees
24 Nov - 25 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.

Holiday Home in Lebanon Springs

8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is NZ$662
includes taxes & fees
1 Dec - 2 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Mobile Home in Chatham

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 NZ$667
includes taxes & fees
25 Nov - 26 Nov
Sugar Shack - 300 square feet of pure sweetness.

Apartment in Hillsdale

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 NZ$297
includes taxes & fees
29 Nov - 30 Nov
The Brooks Motel: Exceptional Suite

Holiday Home in Lee

10.0 out of 10, Exceptional, (4)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
Bungalow in the Berkshires

Cottage in New Lebanon

2.0 star property
The price is NZ$2,975
includes taxes & fees
9 Dec - 10 Dec
Berkshires farm, 30+ guests, 50 acres

Mobile Home in 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 NZ$667
includes taxes & fees
24 Nov - 25 Nov
BLUSH: Boutique TINY home*private spa*walk to town

Holiday Home in Great Barrington

9.2 out of 10, Wonderful, (5)
The price is NZ$526
includes taxes & fees
23 Nov - 24 Nov
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Pittsfield

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 NZ$878
includes taxes & fees
22 Nov - 23 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Holiday Home in Hillsdale

8.4 out of 10, Very good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
The price is NZ$971
includes taxes & fees
6 Dec - 7 Dec
Perfect House In Hillsdale, Brings Friends & Fam

Holiday Home in Sheffield

10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$895
includes taxes & fees
23 Nov - 24 Nov
Cheerful 3-bedroom cottage with woodstove
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 favorite 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 depends 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 NZ$248 per night. Entering your travel dates in the search wizard you might find 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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Glendale is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.