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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 96 Cottages in Old Chatham with updated reviews, rates, and availability.

Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (27)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Family-Friendly Richmond Cottage w/ Private Yard
Property grounds

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Comfortable. Homey. Very well stocked, especially the kitchen. Plenty of room and light. Thank you for our visit. "
Family-Friendly Richmond Cottage w/ Private Yard
Cozy cottage with pool, walking distance to lake
Outdoor pool

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (13)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Rose Cottage
Outdoor dining

Rose Cottage

9.6 out of 10, Exceptional, (5)
"Spent time relaxing working and I can"
Rose Cottage
Beachwood Cottage
Interior

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."
Beachwood Cottage
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Fridge, microwave, stovetop, dishwasher

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Beach nearby, sun loungers

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 out of 10, Exceptional, (9)
"Our family rented this property for a long weekend trip and had a great experience. We enjoyed the beauty of the local area, including some great local restaurants and coffee shops. We were snowed in for one day of our trip and enjoyed the coziness of the property and the full kitchen came in clutch to avoid needing to travel during the storm. "
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield Cottage!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Fridge, microwave, stovetop, dishwasher

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (1)
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"House and property were beautiful, well stocked and perfectly situated close to everything but also quiet and scenic. Owner was fantastic to deal with. She was helpful and accommodating, even had a sweet card and little gift to welcome us. Would definitely stay here again!! "
Cozy Berkshire cottage with fireplace.
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Dining

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Plan your Berkshires by the lake
Exterior

Plan your Berkshires by the lake

Plan your Berkshires by the lake
Fun Getaway Lakehouse in the Hudson Valley
Terrace/patio

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (15)
"Can't say enough about this place. It looked like it was just recently built or renovated, and was very very clean. The place was warm, inviting, and very comfortable for my family of 5. Leticia is amazing, very very responsive and understanding. If you are staying in the area (the lake, skiing, etc.) I would highly recommend this place. We will definitely look to book this place again the next time we go skiing at Catamount."
Fun Getaway Lakehouse in the Hudson Valley
Cottage in the Clouds With Mountain Views
Miscellaneous

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
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy
Interior

Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

3.0 star property
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy
Cozy Catskills Home w/ Pond on 2 Acres!
Terrace/patio

Cozy Catskills Home w/ Pond on 2 Acres!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely gorgeous property, the owner is awesome and can’t forget Leo the cat. "
Cozy Catskills Home w/ Pond on 2 Acres!
Underhill Cottage
Interior

Underhill Cottage

Underhill Cottage
Peaceful Athens Retreat at Sleepy Hollow Lake
House (3 Bedrooms) | Interior

Peaceful Athens Retreat at Sleepy Hollow Lake

3.0 star property
Peaceful Athens Retreat at Sleepy Hollow Lake
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 Old Chatham

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!
Fridge, microwave, oven, stovetop

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is SAR 446
SAR 531 total
includes taxes & fees
14 Apr - 15 Apr
Vacation Village in the Berkshires
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (94)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is SAR 487
SAR 526 total
includes taxes & fees
14 Apr - 15 Apr
Micosta Leisure Inn
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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