Condo vacation rentals in Chatham

Our stay was fantastic for our family of four - more than enough space! The photos don't do it justice; the living room / kitchen / dining / games area is far larger than I expected and we loved the open concept. Bedrooms had large, comfortable beds with extra blankets to keep us warm during the cold weather. Minutes from Hunter Mountain and walkable to Ronnie MacGregor's, M&J Bagel Shop, MaMa's Pizza and Jagerberg Beer Hall. Short drive to other restaurants (Hunter Brewery, Hunter Tavern, Scribner's, etc.). Awesome location to ski and explore the surrounding area. Hanna was incredible responsive and flexible. All around fantastic stay.

This condo is in the perfect spot for those wanting to ski on Hunter Mountain. A short walk and you’re on the slopes. The condo is cozy, perfect for a warm night by the fire. The multiple bathrooms and bedrooms were great. Lots of blankets and amenities. It even had a place to dry your boots and mittens! The host was quick to respond to questions, was great at communicating before the trip as what to expect and what was required in checking out, and she gave us great suggestions for snowshoeing. It was the perfect spot for our weekend getaway.

The condo was very comfortable for our family ski weekend. The extra bed was perfect so my boys had their own sleeping space. It was warm and cozy. The location is an easy & short walk to a green slope (looker's left) so it's very convenient for all ski levels. We hope to go back next year!

A Perfect Stay in a Beautiful Apartment with a Helpful Host! I recently had the pleasure of staying at an incredible Airbnb during my visit to New Paltz. From start to finish, everything about this experience was exceptional, and I cannot recommend it highly enough. First and foremost, our host, Ahava, went above and beyond to ensure our stay was comfortable and memorable. She was always available to answer any questions we had and provided excellent recommendations for local attractions, restaurants, and activities. It truly felt like having a personal concierge! The apartment itself was amazing, situated on a quiet street, and filled with sunlight. It was a short walk from downtown New Paltz with all of its restaurants, bars and coffee shops. Already thinking about when we get back up to the area, and will definitely be staying here again!

What a find! You can’t get any closer to the Capitol!

Ranki was fantastic, great communication, the condo was beautiful, very well equipped, inviting, and feels like home, everything you need, "Bring only your toothbrush" is the truth! Great views of WM, the walking to and from the lodge is KEY! Brand new deck, heated boot shelves, new kitchen, all hits with my family! We will be back! Thanks Randi!!

Great stay for skiing at Jiminey Peak! We would definitely stay here again. Clean, spacious, great location and reasonable price!

We had a wonderful long ski weekend and thoroughly enjoyed this property. Philip was a wonderful and communicative host and we would absolutely come for a visit again. Highly recommended!

We had an amazing stay at Kristen’s condo with our family—my husband, our toddler, and our dog. The location was perfect—secluded and peaceful, but still close to hiking trails and charming small towns. The condo was cozy, clean, and well-equipped with everything we needed for a relaxing weekend. Kristen was responsive and helpful, making our stay even better. Highly recommend for a family getaway!

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Great little ski condo right by the slopes

Well designed, well maintained modern style home. Love the warm toned interior. Quick drive to lots of hiking spots which was what brought us here. Management team was very professional and easy to communicate. Will consider for any future trips to Minnewaska/Mohonk.

Katie's place was great--very stylish, conveniently located, and well maintained/cleaned. Loved the renovation of the older building to create a contemporary space while incorporating some of the historic beams and brick work into the design. The living area and kitchen were spacious, comfortable, and well-appointed. The beds were very comfortable. It was great to have a dedicated parking space. The street is busy and well lit, so we were happy to have ear plugs and eye shades when trying to sleep. The location is convenient to MassMOCA and some great restaurants. All in all, a fantastic stay!

This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!

A beautiful home. Felt comfortable and relaxing. Very well equipped. A nice small outdoor seating area to watch the creek and see wildlife.

Sam was great host super responsive, clean space left us great recommendations to eat and visit.

Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

Hamilton is a wonderful host and the area is always beautiful and fun.

My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

We recently stayed at Andrew's condo, and it was nothing short of amazing! The location couldn't be better – right next to the slopes with easy accessibility to the mountain and the ski rental place. We were a group of two families, totaling 6 kids and 4 adults, and the condo was the perfect accommodation for our ski trip. The kids were thrilled with their bunkbed rooms, each equipped with their own TVs, providing a cozy and entertaining space for them to unwind after a day on the slopes. The condo itself was beautifully decorated, creating a warm and inviting atmosphere. There was plenty of room for all of us to relax and spend quality time together. The highlight for both kids and adults was undoubtedly the hot tub and pool. After a day of skiing, it was pure bliss to soak in the hot tub and enjoy the breathtaking views. A special shoutout to Andrew, our fantastic host! He was incredibly responsive and welcoming, ensuring that our stay was comfortable and stress-free.

We worked through a bit of calendar scheduling snafu quickly. Scott was accommodating, proactive, and responsive. The condo was in a great location, maintained well, and clean. We very much enjoyed our quick weekend getaway. Thank you!

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!