Search and Rent Chatham Condos

Compare 46 Condo Rentals in Chatham with updated reviews, rates, and availability.

Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
Exterior
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
10.0 out of 10, Exceptional, 6 reviews
"The property was as advertised. Clean and comfortable. And right on the mountain - ski-in/ski-out. Perfect for families."
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Beach
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
10.0 out of 10, Exceptional, 33 reviews
"We loved our stay at this beautiful condo. Clean and perfectly suited at the base of Jiminy Peak. Host was responsive and provided excellent detailed instructions."
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Exterior
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
9.8 out of 10, Exceptional, 9 reviews
"The unit was clean and was accurately described on the listing. Check in was easy. This was our second time here and will return again."
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
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Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Exterior
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
10.0 out of 10, Exceptional, 5 reviews
"We love Bentley Brook! We will come back next year!"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Fridge, microwave, oven, stovetop
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
10.0 out of 10, Exceptional, 21 reviews
"I cannot say enough good things about this condo and the host! Colin was so easily reachable and even last minute we were able to add another night onto our stay. We had 2 little ones and 4 adults and we were so comfortable with all the space. Every amenity you think you may need was there, we didn’t find ourselves saying “Oh I wish there was…” one time! It was the perfect location for us while our group was there meeting in that building. The balcony views were phenomenal and if our group comes...
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
9.4 out of 10, Exceptional, 12 reviews
"Justine was a great host, and was quick to respond to all my texts. The condo was clean equipped with the basic amenities. He provided us with a drip coffee machine, but you could also get complimentary Keurig coffee every morning from the lobby. The only small inconvenience to our stay was that there was no heat in the living room, and although there is a vent from the bedroom into the living room, it didn't seem to circulate the warm air from the bedroom into the living room. The front desk...
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, 8 reviews
"Very comfortable and convenient space. It easily accommodated me and my two teenaged children. The proximity to the ski lifts at Jiminy Peak is a great feature."
UNIQUE - 1BR Country Condo @ Jiminy Peak
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
4.0 out of 10, 1 review
"Listing is inaccurate. Clearly said 2 bedrooms in ad., but it is only 1."
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Exterior
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
9.6 out of 10, Exceptional, 7 reviews
"Everything was perfect for a ski weekend"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Snow and ski sports
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
9.6 out of 10, Exceptional, 5 reviews
"Perfect stay at Jiminy Peak. Unit had everything I needed."
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Exterior
Ski In & Ski Out - Deluxe 1 Bedroom Condo
10.0 out of 10, Exceptional, 6 reviews
"We love Jiminy Peak and having a week at a ski-in, ski-out unit was fantastic. We skied back for lunch and skied back out for the afternoon; skied in for a quick dinner and the boys skied back out for night skiing. Terrific location! Kitchen was clean and serviceable (no oven but two burners, sink, dishwasher, microwave, and toaster) and beds were good. Everything was easy... check in, check out, so smooth. A great time was had by all!!!!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Outside Adventure-Skiing, Hiking, and Relaxation
Exterior
Outside Adventure-Skiing, Hiking, and Relaxation
10.0 out of 10, Exceptional, 1 review
"Weather didn't help but the rental and the location were exceptional!"
Outside Adventure-Skiing, Hiking, and Relaxation
Ski on ski off 1 Br loft condo in the village center with private gated parking
Fridge, microwave, oven, stovetop
Ski on ski off 1 Br loft condo in the village center with private gated parking
10.0 out of 10, Exceptional, 13 reviews
"My friends and I were looking for a close escape from Albany, NY. When we entered the condo we immediately felt a sense of ease and once the wood burning fire was started we were in heaven. The condo is in the perfect location within the JP Village. We were able to walk to the Country Store, Bars and Restaurants. What was PERFECT was the close proximity to the lifts; right out the door. We could ski on, ski off and take breaks without dealing with the crowds in the food halls. The condo itself...
Ski on ski off 1 Br loft condo in the village center with private gated parking
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
10.0 out of 10, Exceptional, 1 review
"We very much enjoyed our stay. The place was very comfortable and very clean. The location worked out perfect and the parking was very convenient."
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Exterior
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
10.0 out of 10, Exceptional, 1 review
"great stay as always!"
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Pool
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
10.0 out of 10, Exceptional, 9 reviews
"Love the ski in and out of this property. Family enjoyed staying here, highly recommended."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Perfect for Winter Skiing!!
Fridge, microwave, oven, stovetop
Perfect for Winter Skiing!!
Perfect for Winter Skiing!!
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Exterior
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
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See all available properties in 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 Chatham

Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, 858 reviews
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $159
$174 total
includes taxes & fees
4 Jun - 5 Jun
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony
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 $125
$141 total
includes taxes & fees
4 Jun - 5 Jun
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
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.

Chatham Condo Rentals information

Number of reviews
138
Accommodation
46 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

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What is there to do in Chatham near my condo?
Whatever you’re into, Chatham has plenty of things to capture your imagination. The Mac-Haydn Theatre, Hudson Chatham Winery and Shaker Museum and Library are on many travelers’ sightseeing plans. Don’t forget to explore Kinderhook Lake, Van Alen House and High Falls Trail either. With Expedia’s condo deals in Chatham, you can discover even more awesome attractions like these with the cash you save.

Recent reviews of Chatham hotels
Expedia 亿客行 verified reviews

Quality Inn

Quality Inn

5/5 Excellent
Birthday Trip
"Our stay was excellent. I greatly appreciated the refrigerator and microwave in the room. The proximity to everything in Lee was marvelous."
A verified traveler stayed at Quality Inn
Posted 13 hours ago
Quality Inn