Glendale Vacation Rentals

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Mar 27 - Mar 29

Vacation Rentals in Glendale

Fridge, microwave, oven, stovetop
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.
$183 nightly
The price is $195
Dec 8 - Dec 9
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

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.
$185 nightly
The price is $203
Dec 8 - Dec 9
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! 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.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$189 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Home in Great Barrington
Exterior
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, (34)
"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.
$375 nightly
The price is $419
Dec 8 - Dec 9
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

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.
$164 nightly
The price is $184
Dec 12 - Dec 13
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
$332 nightly
The price is $372
Dec 9 - Dec 10
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Interior
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.
$255 nightly
The price is $283
Dec 22 - Dec 23
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

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.
$217 nightly
The price is $242
Dec 8 - Dec 9
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio
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.
$332 nightly
The price is $374
Dec 10 - Dec 11
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Dining
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.
$640 nightly
The price is $715
Dec 9 - Dec 10
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$404 nightly
The price is $451
Dec 8 - Dec 9
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 8 - Dec 9
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

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.
$461 nightly
The price is $517
Dec 8 - Dec 9
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Exterior
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

2.0 star property
New Lebanon
$1,956 nightly
The price is $1,983
Jan 7 - Jan 8, 2026
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
Fridge, microwave, oven, stovetop
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!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$441 nightly
The price is $493
Dec 8 - Dec 9
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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, (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.
$303 nightly
The price is $342
Dec 9 - Dec 10
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Outdoor spa tub
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.
$366 nightly
The price is $413
Dec 14 - Dec 15
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Exterior
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, (1)
"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
Dec 8 - Dec 9
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"We stay here every year and it never disappoints "
Elizabeth 4-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington 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 $283 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?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental near 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 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.