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Compare 44 Cottages in Berlin with updated reviews, rates, and availability.

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
Cozy cottage with pool, walking distance to lake
Dining
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (12)
"This was our second year in a row here! We already booked for next summer! Peaceful and calm. The pool is fantastic."
Cozy cottage with pool, walking distance to lake
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.
Great Place to get away and have clean fresh air surround you!
Book now for a magical & peaceful fall stay before its too late!
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (130)
"We enjoyed our stay. It was a beautiful cottage on a very nice pond. We enjoyed kayaking, eating our meals on the deck overlooking the water, and enjoying a fire every night. It also was only a couple hours away from Fort Ticonderoga, so we enjoyed going there one day. "
Great Place to get away and have clean fresh air surround you!
Perfect for a peaceful get away in clean fresh Vermont air!
Newly sided entire house and garage
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (69)
"The Honey Bear Cottage is adorable. The cottage is well stocked and immaculate. The adjustable bed is extremely comfortable. We did not get to use the fire pits or the upstairs bedroom but we did get to enjoy Big Pond, using the kayak and pedal boat. The hostess, Linda Jane is very attentive to your needs. Watching the stars from the deck is amazing. I would love to stay again. Very relaxing!"
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
Livingroom - Woodburning stove and sleeper double size pull out couch.
Lake life at Woodford Cottage
9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
Morgan House on Crooked Lake
Private kitchen
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
"Beautiful home on water. Perfect place to have family gatherings! Looking forward to another visit. Best area for pizza, too! ( Kay’s)"
Morgan House on Crooked Lake
Spacious Historic Home in the Berkshires!
Property grounds
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
Terrace/patio
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
3.0 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
Charming Albany Retreat ~ 3 Mi to Downtown!
Living area
Charming Albany Retreat ~ 3 Mi to Downtown!
3.0 star property
Charming Albany Retreat ~ 3 Mi to Downtown!
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
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Living area
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
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!
Pet-friendly Latham Retreat ~ 7 Mi to Albany!
Exterior
Pet-friendly Latham Retreat ~ 7 Mi to Albany!
3.0 star property
Pet-friendly Latham Retreat ~ 7 Mi to Albany!
Chic Troy Home Near Downtown, 9 Mi to Albany!
Living area
Chic Troy Home Near Downtown, 9 Mi to Albany!
3.0 star property
8.0 out of 10, Very Good, (1)
Chic Troy Home Near Downtown, 9 Mi to Albany!
Eclectic Troy Home w/ Hot Tub - Pet Friendly!
Dining
Eclectic Troy Home w/ Hot Tub - Pet Friendly!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This place is awesome. We weren't there much as it was parents weekend for RPI but it was so great to come back to a house with a hot tub and sauna. I thought we would use the pool table but the weekend ended up too busy to invite friends over. Super comfortable and beautiful."
Eclectic Troy Home w/ Hot Tub - Pet Friendly!
Peaceful Family Home w/ Fire Pit & Large Yard
Terrace/patio
Peaceful Family Home w/ Fire Pit & Large Yard
3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Bennington Gem w/ Smart TV Near Historic District!
Property grounds
Bennington Gem w/ Smart TV Near Historic District!
3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!
Family-Friendly Richmond Cottage w/ Private Yard
Richmond Vacation Rental | 2BR | 2BA | 1,750 Sq Ft | Stairs Required
Family-Friendly Richmond Cottage w/ Private Yard
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great house in a beautiful location, all the amenities for kids and adults, and very clean! Highly recommended!"
Family-Friendly Richmond Cottage w/ Private Yard
Riverfront A-frame Cabin in Troy w/ Pool & Dock!
Living area
Riverfront A-frame Cabin in Troy w/ Pool & Dock!
3.0 star property
Riverfront A-frame Cabin in Troy w/ Pool & Dock!
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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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Other property types in Berlin

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is SAR 633
SAR 732 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is SAR 549
SAR 602 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Living room with wood-burning stove
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (208)
"Unique and secluded spot close to Bennington area attractions "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
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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