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Compare 391 Vacation Homes in Old Chatham with updated reviews, rates, and availability.

Vacation home just 11 minutes from MVP Arena
Kitchen
Vacation home just 11 minutes from MVP Arena
2.0 star property
9.4 out of 10, Exceptional, (9)
"Nice place "
Vacation home just 11 minutes from MVP Arena
Mini Mansion newly furnished with Italian furniture 8kslim televisions all rooms
Exterior
Mini Mansion newly furnished with Italian furniture 8kslim televisions all rooms
9.6 out of 10, Exceptional, (10)
"We had a mini Family Reunion in the Albany area so 10 of us stay at this spacious home. Plenty of sleeping capability and bathrooms to accommodate all of us. The back patio and fire pit was a real treat as the evening got cooler. Location was super as we had many flying into Albany Intl Airport. We had a great golf tournament at Frear Park Golf Course. With the foliage changing and nice weather - it was perfect! Thanks for letting us stay with you! "
The price is SAR 1,458
SAR 2,311 total
includes taxes & fees
18 Nov - 19 Nov
Mini Mansion newly furnished with Italian furniture 8kslim televisions all rooms
Home away from home
Private kitchen
Home away from home
8.4 out of 10, Very Good, (13)
"Property was in good shape, though I recommend the owner consider refinishing the tub, the current paint job is not so good. The location is too far from downtown Troy to easily walk but is an easy drive. The building has multiple units and finding the right one was a bit tricky, but the place was clean and well-kept overall and parking was easy, I would stay again."
Home away from home
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is SAR 984
SAR 2,014 total
includes taxes & fees
18 Nov - 19 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is SAR 710
SAR 1,384 total
includes taxes & fees
16 Nov - 17 Nov
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Summertime
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
10.0 out of 10, Exceptional, (46)
"We were very happy with our stay. The house was as described and pictured in the listing. Well stocked for our needs, spare toothbrush, coffee, etc. Would definitely stay again!"
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Large lakeside yard and patio area
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
10.0 out of 10, Exceptional, (49)
"We had such a great time at this house with our family. We were able to check in early and the place was clean and packed full of supplies for us to use during our stay such as plates, napkins, shampoo/conditioner, hair dryer, coffee, etc.! We brought fishing rods and fished off the dock. We also used the kayaks to go out on the lake and it was so much fun! Anytime we messaged Michael and Beverly they responded within minutes! We were able to check out late and it was the easiest check out I’ve...
The price is SAR 1,127
SAR 1,920 total
includes taxes & fees
17 Nov - 18 Nov
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Secluded Family Home in Serene Stockbridge Woods
Living area
Secluded Family Home in Serene Stockbridge Woods
10.0 out of 10, Exceptional, (18)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.
Private kitchen
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (223)
"One of the best properties i've ever stayed at "
The price is SAR 492
SAR 768 total
includes taxes & fees
18 Nov - 19 Nov
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Welcome to River House!
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Amazing Entertainment Space
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (134)
"Everything about this property makes it a wonderful get-away … gorgeous woodland and trails on property, quiet and remote but with all the comforts of a spacious home. The barn renovation is perfect - the right balance of original charm and modern amenities. The hot tub and sauna, and outdoor fire pit, made it a 100% fun and relaxing weekend for my family. This property truly is a slice of paradise! "
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (35)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Modern-Chic Athens Home - Fish, Ski & Swim!
Athens Vacation Rental | 5BR | 2.5BA | 2,800 Sq Ft | 1 Step to Enter
Modern-Chic Athens Home - Fish, Ski & Swim!
10.0 out of 10, Exceptional, (14)
"Our group of 12 had a great stay at the house. There was plenty of room for us all with the spacious bedrooms and 2 living room areas. We had 2 kids use the floor mattresses which worked well for them. The house was clean, kitchen well stocked, grill was easy to use, very close walk to the pool and beach areas. Lastly, the owner Alex was very easy to communicate with and answered questions right away. Highly recommend this house!"
Modern-Chic Athens Home - Fish, Ski & Swim!
Expansive Upstate Home w/ Home Theater!
East Schodack Vacation Rental | 5BR | 2.5BA | Stairs Required To Access
Expansive Upstate Home w/ Home Theater!
10.0 out of 10, Exceptional, (12)
"Owner was very responsive. House was spacious with everything we could have needed. Back yard and theater was amazing. 10 out of 10 recommend"
Expansive Upstate Home w/ Home Theater!
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Exterior
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (31)
"The castle house is fantastic. Spacious, beautifully decorated and equipped. There is no meal you can't craft from this kitchen. The house is super quiet,the beds are comfy, towels plush...close to Great Barrington. I can't say enough good things. Book it."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Cozy log cabin in Lake Community.
Terrace/patio
Cozy log cabin in Lake Community.
10.0 out of 10, Exceptional, (18)
"It was quiet, cozy, spacious and clean!! So very inviting and we did not want to leave!!"
Cozy log cabin in Lake Community.
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
the house
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
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 One-of-a Kind Estate! Pool, Gym, Trails! 100 per person for 8+guests!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
Beautiful One-of-a Kind Estate! Pool, Gym, Trails! 100 per person for 8+guests!
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful One-of-a Kind Estate! Pool, Gym, Trails! 100 per person for 8+guests!
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is SAR 634
SAR 733 total
includes taxes & fees
25 Nov - 26 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is SAR 560
SAR 614 total
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Mountain Resort
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.