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Glendale Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Glendale vacation rentals

TV, fireplace, DVD player, books

Hudson Valley Multi-Unit Escape: Secluded + Scenic

Hudson Valley Multi-Unit Escape: Secluded + Scenic
Claverack
$915 nightly
The price is $1,025
Jul 23 - Jul 24
Total with taxes and fees
Hudson Valley Multi-Unit Escape: Secluded + Scenic
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, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
$419 nightly
The price is $468
Jul 15 - Jul 16
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
Cheerful 3-bedroom cottage with woodstove
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$283 nightly
The price is $316
Jul 27 - Jul 28
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$432 nightly
The price is $483
Jul 28 - Jul 29
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
$306 nightly
The price is $342
Jul 16 - Jul 17
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (12 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.
$629 nightly
The price is $703
Jul 16 - Jul 17
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
$648 nightly
The price is $685
Jul 15 - Jul 16
Total with taxes and fees
Treetop Hideaway in Tyringham
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (9 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
$341 nightly
The price is $382
Jul 15 - Jul 16
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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
$499 nightly
The price is $554
Jul 15 - Jul 16
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
$1,189 nightly
The price is $1,328
Jul 22 - Jul 23
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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.
$407 nightly
The price is $454
Jul 28 - Jul 29
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
$981 nightly
The price is $1,096
Jul 19 - Jul 20
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Beach nearby

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
$571 nightly
The price is $638
Aug 6 - Aug 7
Total with taxes and fees
Beachwood Cottage
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
$380 nightly
The price is $425
Jul 20 - Jul 21
Total with taxes and fees
stylish Berkshires Retreat
Smart TV, books

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very Good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
Spacious Central Berkshires Home for Groups
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,060 nightly
The price is $1,149
Jul 15 - Jul 16
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
$170 nightly
The price is $190
Jul 15 - Jul 16
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
$351 nightly
The price is $392
Jul 19 - Jul 20
Total with taxes and fees
Home in Great Barrington
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-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Very nice and clean hotel for an overnight stay passing through Massachusetts. Located off a very busy road so pulling out of the parking lot can be difficult."
Timothy 1-night trip
Posted 7 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Glendale

Everything you need to know about Glendale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Glendale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Glendale vacation 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 low season months. For more hustle and bustle, you may prefer to visit Glendale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $316 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Glendale rentals

At Expedia, we put the best Glendale vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Cozy Riverside Berkshires Retreat: This vacation home rental near Glendale is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Glendale?

Choose from 5 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 Bousquet Ski Area, 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.