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Browse Select Old Chatham Holiday Homes

Home away from home
10.0 out of 10, Exceptional, 5 reviews
"nice and quiet location. Close to alot of good food places. Great location for the things we came to do."
Home away from home
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 66 reviews
"Probably one of the cleanest places I have ever stayed. The house is perfect. Beautiful views!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, 97 reviews
"Lovely chalet by the lake, we had such a relaxing stay. The place is just like on the pictures, very quiet but not far from amenities. The host are very friendly super responsive. Thanks for having us!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
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Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
10.0 out of 10, Exceptional, 7 reviews
"Le Soleil Suite was just as it was pictured. It was very pretty, neat and clean. Sarah provided everything that we needed for our stay and she was very responsive if we had any questions.It was so quiet and peaceful. We truly enjoyed our stay!"
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, 31 reviews
"My family and I came in for a wedding weekend. The property was clean and spacious. We all really enjoyed"
Cozy Retreat on Copake Lake in our Charming Home
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, 11 reviews
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
The price is £870
per night
4 Jun - 5 Jun
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, 128 reviews
"Our stay at The Barn in New York was unforgettable. This luxury home, converted from a barn and situated at the end of a back road, is surrounded by 50 acres of picturesque fields and has every amenity. With many restaurants a short drive away and only 20 minutes to Great Barrington, MA, and Hudson, NY, we were never short on dining options and The Prairie Whale was our favorite and also dog friendly. The area offered endless adventures with hiking trails, antique stores, galleries, and outdoor...
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is £268
per night
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests!
9.4 out of 10, Exceptional, 88 reviews
"Comfortable, easy to get to, stocked with the all basics that you need. Comfy beds, all good."
PRISTINE CAPE COD ON THE CREEK! 4 Large Bedrooms - 8 Guests!
4 Bdrm Modern Victorian with Tree House and playground
9.8 out of 10, Exceptional, 97 reviews
"Great house for our family to stay for my son’s graduation. Galina was wonderful to work with! I highly recommend!"
4 Bdrm Modern Victorian with Tree House and playground
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, 105 reviews
"We attended our daughters wedding in Philmont. House was perfect. Views were amazing! Enjoyed morning walks and sitting outside on the deck. Very tranquil!"
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
✨Spacious Urban APT w/4BR & Office-Ready in Albany
10.0 out of 10, Exceptional, 22 reviews
"Property was in a great location, nice neighborhood for our long family weekend. We had a wedding, commissioning, and graduation ."
The price is £243
per night
10 Jun - 11 Jun
✨Spacious Urban APT w/4BR & Office-Ready in Albany
Historic New Lebanon Hideaway on 33 Private Acres!
10.0 out of 10, Exceptional, 1 review
Historic New Lebanon Hideaway on 33 Private Acres!
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
10.0 out of 10, Exceptional, 3 reviews
"Our family had the pleasure of staying at this home during our child’s graduation from the nearby Berkshire school. It was the perfect situation for us in an idyllic setting very close to the campus. The home is over 250 years old and has been lovingly updated. The kitchen has seemingly all new appliances and gorgeous wood plank countertops with an adjacent windowed sitting area with a large hearth. The old and new are beautifully combined. Our family members spent a lot of time looking at the...
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Berkshire Manor for Lasting Memories
10.0 out of 10, Exceptional, 2 reviews
"Leah was a wonderful host to us. She provided easy-to-follow instructions for getting into the house, offered good suggestions on things to do and where to eat. Although the house was a bit larger than we needed, we chose it because of the location, the generous sized and comfortable looking (from photos) casual spaces, the kitchen and the number of bathrooms so we each had our own. This house did not disappoint! It has lots of New England charm, the beds were comfortable, as were the several...
Berkshire Manor for Lasting Memories
Sleepy Hollow Lake Home w/ Deck, Pool Access!
10.0 out of 10, Exceptional, 2 reviews
"We had a wonderful stay. House is brand new, super clean and bright. We loved the access to bikes, plus tennis, pool, and the lake. Will definitely return!"
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
The price is £614
per night
4 Jun - 5 Jun
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, 8 reviews
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, 12 reviews
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
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See all available properties in Old Chatham
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.

Other property types in Old Chatham

Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, 79 reviews
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 858 reviews
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"
The price is £137
per night
4 Jun - 5 Jun
Jiminy Peak Mountain Resort
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, 73 reviews
"Expedia said they have a Sunday buffet, but they didn't."
The price is £111
per night
5 Jun - 6 Jun
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.

Old Chatham Holiday Homes information

Number of reviews
653
Accommodation
349 Holiday Homes
Lowest Price
£243
Highest Price
£870

Old Chatham Hotel Reviews
Expedia verified reviews