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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 117 Cottages in Chatham with updated reviews, rates, and availability.

Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (104)
"Great hosts who made our stay enjoyable. Very peaceful location. "
Quiet rustic cottage with shared lake access
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Interior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"Stayed with family for a wedding nearby and had a great experience. Nice house, clean and comfortable and as advertised. Very comfortable bed. Remote location so it’s quiet and peaceful, and short walk to lake. Host was very helpful and quick to respond. Would stay again!"
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
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)
"Very nice and cozy and comfortable! "
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)
"Excellent property: would have liked to stay longer. "
Family-Friendly Richmond Cottage w/ Private Yard
Loblolly Cottage - Enchanting Retreat set among towering pines.
Terrace/patio

Loblolly Cottage - Enchanting Retreat set among towering pines.

10.0 out of 10, Exceptional, (37)
"My wife and I had a wonderful stay. Super cozy, romantic and accommodating. We had a wonderful time and William was very responsive. Would highly recommend and stay again. "
Loblolly Cottage - Enchanting Retreat set among towering pines.
Cozy cottage with pool, walking distance to lake
Outdoor pool

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (14)
"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
Rose Cottage
Exterior

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It was a beautiful location which gave me a chance to reset and decompress I had access to all the nearby attractions such as Wyndham Hunter and castigger falls"
Rose Cottage
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is SAR 750
SAR 1,542 total
includes taxes & fees
27 Apr - 28 Apr
The Blue Elm - A Historic Berkshire Cottage
Beachwood Cottage
Fridge, microwave, stovetop, coffee/tea maker

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
Charming Cottage in the Heart of Catskill & Pet Friendly
Smart TV

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (12)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (9)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Lake Views & Dock Access - Pittsfield Cottage!
TV, fireplace

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!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Property grounds

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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, (2)
"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.
Property grounds

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Interior

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)
"We enjoyed our stay with friends. Conveniently located near the water, great amenities and very clean. The host was incredibly responsive and kind throughout!"
Fun Getaway Lakehouse in the Hudson Valley
Vintage Country Home with Games, BBQ & Trails, & 20 Min to Hudson
Fridge, microwave, oven, stovetop

Vintage Country Home with Games, BBQ & Trails, & 20 Min to Hudson

10.0 out of 10, Exceptional, (2)
"Absolutely beautiful location. Lots of hiking nearby. Countless places, towns, attractions, etc. to check out. The house was better than the pictures suggest. We are already making plans to return in the Spring / Summer."
Vintage Country Home with Games, BBQ & Trails, & 20 Min to Hudson
Cottage in the Clouds With Mountain Views
Exterior

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
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 Chatham

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1799)
"Always a great place to stay!!"
The price is SAR 348
SAR 422 total
includes taxes & fees
8 May - 9 May
Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.6 out of 10, Excellent, (9)
"We always live these cabins & we've been coming for years!"
The price is SAR 469
SAR 648 total
includes taxes & fees
30 Apr - 1 May
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is SAR 487
SAR 526 total
includes taxes & fees
11 May - 12 May
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.