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Check prices for these dates

Next weekend
24 Muh. - 26 Muh.
In two weeks
31 Muh. - 2 Saf.
In one month
14 Saf. - 16 Saf.
In two months
14 Rab. I - 16 Rab. I

Compare 78 Cottages in Old Chatham with updated reviews, rates, and availability.

Cozy cottage with pool, walking distance to lake
Private kitchen

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
Cozy Berkshire cottage with fireplace.
Interior

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (23)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
Cozy Berkshire cottage with fireplace.
Welcome to the Red Bridge Cottage!
Cozy cottage with glass door pellet stove & whirlpool tub for those snowy nights

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Richmond Vacation Rental | 3BR | 2BA | Steps to Enter | 1,210 Sq Ft

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!
Charming Cottage in Private Lake Community (Pet-Friendly!)
Welcome to White Bunny Cottage

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

9.8 out of 10, Exceptional, (26)
"Our family (7 adults and 2 dogs) stayed over the Christmas holiday. The house was just perfect for our group. It was clean, comfortable and cozy! The hosts were responsive and super nice to deal with. We would definitely go back for any future stays in the area. "
Charming Cottage in Private Lake Community (Pet-Friendly!)
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, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
The gorgeous view from our back yard and note the firepit!

Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!

9.8 out of 10, Exceptional, (6)
"Our family of four stayed here for the weekend after picking up our daughter from Hawthorne Valley Farm Camp, and this property was perfect for us! The home was immaculate and cool when we arrived. Rudy communicated a few days ahead of time about an issue with the fridge and provided coolers and ice for us to use. We loved eating dinner out on the porch and playing board games down in the media room. The beds were clean and comfortable without being too soft. It made a huge difference that our...
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
Rose Cottage
Private kitchen

Rose Cottage

9.6 out of 10, Exceptional, (5)
"Spent time relaxing working and I can"
Rose Cottage
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, (14)
"Beautiful clean property. A lovely location. Exceeded expectations."
Fun Getaway Lakehouse in the Hudson Valley
15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake
Private kitchen

15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake

10.0 out of 10, Exceptional, (8)
"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."
15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake
Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD
Relax on the large deck with lake views

Cozy Hudson Valley Lake Cottage :CATAMOUNT SKI/SNOW BOARD

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 :CATAMOUNT SKI/SNOW BOARD
Beachwood Cottage
Exterior detail

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
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!
Cozy Catskills Home w/ Pond on 2 Acres!
Living area

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!
Spacious Historic Home in the Berkshires!
Property grounds

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior

A Charming Cottage - Secluded in Nature and Relaxing

10.0 out of 10, Exceptional, (3)
"The rental was nice. It was convenient for viewing the fall foliage and just enjoying the countryside. "
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'
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!
Underhill Cottage
Interior

Underhill Cottage

Underhill Cottage
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!
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

Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends

Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!

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!"
Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1756)
"Room was right across from the pool. Beautiful view of the mountain five min drive to the base. Beautiful pool and outdoor jacuzzi. Had an amazing stay! Cant wait to go back!"
The price is SAR 703
SAR 809 total
includes taxes & fees
20 Jan - 21 Jan
Vacation Village in the Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (32)
"We had such a lovely time at this property! The space is gorgeous and the outside is perfect for walking around and exploring with the dogs. We had 18 people staying overnight and we all fit well (with the addition of some curtains for privacy) and had our own space to hide away in when needed. It was stocked with pretty much everything we needed, including firewood, glass vases for wedding decorations, tons of dishware, throw blankets, etc. Our group made wonderful memories here - thank you!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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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