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Glendale Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Glendale vacation rentals

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.
The price is SAR 953
SAR 1,924 total
includes taxes & fees
12 Jul - 13 Jul
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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.
The price is SAR 794
SAR 1,722 total
includes taxes & fees
13 Jul - 14 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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
The price is SAR 563
SAR 715 total
includes taxes & fees
12 Jul - 13 Jul
The Brooks Motel: Exceptional Suite
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
The price is SAR 841
SAR 2,081 total
includes taxes & fees
15 Jul - 16 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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.
The price is SAR 676
SAR 1,476 total
includes taxes & fees
22 Jul - 23 Jul
stylish Berkshires Retreat
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is SAR 522
SAR 1,497 total
includes taxes & fees
22 Jul - 23 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is SAR 661
SAR 2,111 total
includes taxes & fees
13 Jul - 14 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is SAR 864
SAR 1,426 total
includes taxes & fees
12 Jul - 13 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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.
The price is SAR 831
SAR 1,277 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Riverside Berkshires Retreat
Dining

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
The price is SAR 507
SAR 780 total
includes taxes & fees
16 Jul - 17 Jul
Charming Apt in 18th c Berkshire Farmhouse
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.
The price is SAR 727
SAR 1,638 total
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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.
The price is SAR 1,502
SAR 2,638 total
includes taxes & fees
12 Jul - 13 Jul
Guesthouse Cabin vacation rentals in Berkshire County
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, (7 reviews)
BLUSH: Boutique TINY home*private spa*walk to town
Pool

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is SAR 807
SAR 1,497 total
includes taxes & fees
15 Jul - 16 Jul
Hudson NY’S Country Serenity Guest 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.
The price is SAR 1,081
SAR 1,619 total
includes taxes & fees
16 Jul - 17 Jul
Home in Great Barrington
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.
The price is SAR 1,314
SAR 2,395 total
includes taxes & fees
6 Aug - 7 Aug
Beachwood Cottage
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
The price is SAR 890
SAR 1,883 total
includes taxes & fees
12 Jul - 13 Jul
Cheerful 3-bedroom cottage with woodstove
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"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 SAR 976
SAR 1,257 total
includes taxes & fees
20 Jul - 21 Jul
Sugar Shack - 300 square feet of pure sweetness.
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.
The price is SAR 1,378
SAR 2,572 total
includes taxes & fees
13 Jul - 14 Jul
Treetop Hideaway in Tyringham
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
Michael 1-night trip
Posted 1 hour ago
The Yankee Inn

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.