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Glendale Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Glendale vacation rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,255 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
$115 nightly
The price is $128
Dec 3 - Dec 4
Total with taxes and fees
Berkshire Mountain Lodge
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
$96 nightly
The price is $107
Nov 11 - Nov 12
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

3. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$247 nightly
The price is $276
Nov 9 - Nov 10
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

4. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
$264 nightly
The price is $295
Nov 8 - Nov 9
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
A dining area with a wooden table, chairs, and a ceiling fan.

5. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
$270 nightly
The price is $301
Nov 8 - Nov 9
Total with taxes and fees
Leaf-Peeper Paradise in the Berkshires
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

6. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$194 nightly
The price is $196
Nov 5 - Nov 6
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

7. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
$1,185 nightly
The price is $1,300
Nov 11 - Nov 12
Total with taxes and fees
Beautiful and Private Home Centrally Located in the Berkshires
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
$289 nightly
The price is $323
Nov 9 - Nov 10
Total with taxes and fees
Home in Great Barrington
A sandy beach with a lake and forest in the background.

9. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$291 nightly
The price is $325
Nov 9 - Nov 10
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A spacious living room with a dining area, a kitchen, and a large window.

10. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$210 nightly
The price is $212
Nov 5 - Nov 6
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

11. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
$550 nightly
The price is $614
Nov 9 - Nov 10
Total with taxes and fees
Secluded Family Home in Serene Stockbridge Woods
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

12. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
$604 nightly
The price is $663
Nov 9 - Nov 10
Total with taxes and fees
Ellie’s Overlook, best view in the Berkshires!
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

13. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$738 nightly
The price is $824
Nov 23 - Nov 24
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A living room with a sofa, armchairs, a coffee table, and a television.

14. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
$538 nightly
The price is $601
Nov 5 - Nov 6
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

15. 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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$320 nightly
The price is $357
Nov 5 - Nov 6
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a sofa, armchair, coffee table, and TV.

16. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
$509 nightly
The price is $568
Nov 5 - Nov 6
Total with taxes and fees
Spacious Central Berkshires Home for Groups
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

17. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$597 nightly
The price is $667
Nov 16 - Nov 17
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A hot tub with a string of lights above it, set against a dark night sky.

18. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$335 nightly
The price is $374
Nov 5 - Nov 6
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

19. 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
$191 nightly
The price is $214
Nov 5 - Nov 6
Total with taxes and fees
The Brooks Motel: Exceptional Suite
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

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"It was ok. Breakfast was average."
Ian 1-night trip
Posted 9 hours ago
Quality Inn Lee - Lenox South

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 $107 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home near Glendale is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Glendale?

Choose from 3 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.