Search Cottages in Glendale

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 80 Cottages in Glendale with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....
Aerial view
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental | Studio | 1BA | 800 Sq Ft | Steps to Enter
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (3)
"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."
The price is AED 918
AED 1,875 total
includes taxes & fees
24 Sep - 25 Sep
Beachwood Cottage
Charming historic cottage on scenic road to Mt. Greylock
Summer
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (101)
"We spent three nights in the Stone Schoolhouse, hiking, visiting The Clarke, and enjoying a lovely evening concert at Tanglewood. Convenient location for seeing the Berkshires, unique quarters and friendly hosts. Highly recommend!"
Charming historic cottage on scenic road to Mt. Greylock
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (11)
"Beautiful house with amazing views. Very clean, all brand new. Great location. We would rent it again. Had an amazing Labor Day weekend. Thank you!"
Fun Getaway Lakehouse in the Hudson Valley
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (21)
"We had a wonderful time in Pittsfield for the Holidays. Sarah sent me a few different activities prior to our visit so I could plan some local holiday events ahead of time which was WONDERFUL! They were always responsive if there was an issue or question and the house was perfect."
Cozy Berkshire cottage with fireplace.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Aerial view
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
8.4 out of 10, Very Good, (5)
"We had a lovely two weeks at the Pfeifer cottage. Everything was as promised. The location was quiet, but easy access to Great Barrington and Tanglewood. Two of our grandkids visited and they were in love with the spiral staircase! We way come back again someday."
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
The Blue Elm - A Historic Berkshire Cottage
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (5)
"Beautifully kept, quaint little space - perfect for a relaxing getaway with a small family/friend group or two couples. Very private even though it was in back of the owners' property. The space was thoughtfully arranged and had one of the most in-depth guides to the property and surrounding areas we've ever seen! Nick and Tiffany were great hosts - I would be surprised if they didn't work in hospitality. I would go back."
The price is AED 918
AED 1,727 total
includes taxes & fees
14 Oct - 15 Oct
The Blue Elm - A Historic Berkshire Cottage
Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (98)
"Great property, just as it looked in the images."
Quiet rustic cottage with shared lake access
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Relax on the large deck with lake views
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Historic Home in the Berkshires!
Property grounds
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Beautiful Berkshires Cottage on Lake Buel
Great Barrington Vacation Rental | 3BR | 2.5BA | 2,000 Sq Ft | Steps Required
Beautiful Berkshires Cottage on Lake Buel
10.0 out of 10, Exceptional, (1)
"I’ve been visiting the Berkshires for decades and never stayed at a place with such an amazing view of Lake Buel! Sunrise right from my bed. The house was stocked with everything that was needed for an amazing weekend. Wonderful place to stay!"
Beautiful Berkshires Cottage on Lake Buel
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
New Marlborough Vacation Rental | 1BR | 1BA | 750 Sq Ft | Stairs Required
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (35)
"Quiet apot even when boaters were using the lake. Had a couple of issues that were addressed quickly."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior
A Charming Cottage - Secluded in Nature and Relaxing
10.0 out of 10, Exceptional, (2)
"I’ve been dreaming of a NYC getaway for years and fell in love with this home!!! I love the cozy feeling of being in such magical woods with such a beautiful lake nearby. Having access to the teepee was so special and added even more character. The beds are soooo comfortable I can’t wait to go back!!!"
A Charming Cottage - Secluded in Nature and Relaxing
Waterfalls and Trails at 'the Mills At Green Hole'
Exterior
Waterfalls and Trails at 'the Mills At Green Hole'
3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Underhill Cottage
Interior
Underhill Cottage
Underhill Cottage
Cottage in the Clouds With Mountain Views
Fully stocked kitchen. Two skylights provide plenty of natural light
Cottage in the Clouds With Mountain Views
9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required
Picturesque Cottage with Sunroom on Ashmere Lake!
9.4 out of 10, Exceptional, (20)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Don't see what you're looking for?
See all available properties in Glendale
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Glendale

Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
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.