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Gorgeous large renovated historic home on 10 acres with pool

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A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a dining area with a wooden table and chairs.
A rectangular swimming pool with a stone deck, surrounded by a metal fence, and trees with autumn foliage in the background.
A two-story house with a gabled roof, surrounded by lush greenery and trees.
A stream with a dog playing in the water, surrounded by autumn leaves.
A bedroom with a large bed, a wooden bench, a chair, a bedside table, and a lamp. There are two windows with blinds, a bookshelf, and a small table.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Private pool
  • Dog-friendly
  • Toys
  • Barbecue grill
  • Air-conditioning

Explore the area

View in a map
Chatham, NY
  • Place, The Mac-Haydn Theatre
    ‪7 min drive‬
  • Place, Hudson Chatham Winery
    ‪10 min drive‬
  • Place, Art Omi International Arts Center - Fields Sculpture Park
    ‪15 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪21 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed and 1 Double Sofa Bed

Bedroom 4

3 Single Beds

Bedroom 5

1 Queen Bed

Common area 1

2 Double Futons

Common area 2

2 Double Futons

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Toilet

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden

Add dates for prices

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About the area

Chatham

Located in Chatham, this holiday home is in a rural area. Van Alen House and Martin Van Buren National Historic Site are local landmarks, and the area's natural beauty can be seen at Hand Hollow State Forest and Hand Hollow Conservation Area. Consider Roe Jan Brewing Co. for a night out or Omi International Arts Center if you're travelling with kids. Explore all the area has to offer with hiking/biking trails and cycling.
View more Holiday homes in ChathamOpens in a new window
Map
Chatham, NY

What's nearby

  • The Mac-Haydn Theatre - 7 min drive - 8.5 km
  • Hudson Chatham Winery - 10 min drive - 13.2 km
  • Omi International Arts Center - 15 min drive - 16.4 km
  • Art Omi International Arts Center - Fields Sculpture Park - 15 min drive - 16.4 km
  • Norman Rockwell Museum - 20 min drive - 31.0 km

Getting around

  • Hudson Station - 25 min drive
  • Hudson, NY (HCC-Columbia County) - 19 min drive

Restaurants

  • ‪Stewart's Shops - ‬5 min drive
  • ‪Dairy Queen - ‬6 min drive
  • ‪Yiannis - ‬6 min drive
  • ‪Gnome Slice - ‬6 min drive
  • ‪Our Daily Bread Deli - ‬5 min drive

Frequently asked questions

Does Gorgeous large renovated historic home on 10 acres with pool have a pool?

Yes, this property has an outdoor pool.

Is Gorgeous large renovated historic home on 10 acres with pool pet-friendly?

Yes, this property allows dogs (limit 3 total).

How much is parking at Gorgeous large renovated historic home on 10 acres with pool?

On-site parking is available at the property.

What time is check-in at Gorgeous large renovated historic home on 10 acres with pool?

Check-in begins at 4:00 PM.

What time is check-out at Gorgeous large renovated historic home on 10 acres with pool?

Checkout is at 11:00 AM.

Where is Gorgeous large renovated historic home on 10 acres with pool located?

Located in a rural location, this family-friendly holiday home is within 9 mi (15 km) of The Mac-Haydn Theatre, Omi International Arts Center and Art Omi International Arts Center - Fields Sculpture Park. Ebenezer II Gifts and Antiques and Charles H. Baldwin & Sons are also within 12 miles (20 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 32 out of 35 reviews
Rating 8 - Good. 2 out of 35 reviews
Rating 6 - Okay. 1 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent! Caleb was superb. The house is a gem! We loved the pool and were enchanted by the gardens and grounds. A truly extraordinary stay!
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for a bunch of college friends getting together for a long weekend. Downtown Chatham is charming and friendly with yummy lunch spots like Fork and Whisk and Fiesta Cafe. We happened to be there during the Film Columbia 2026 Film Festival and caught a terrific indie film for a rainy day activity at the lovely Crandell Theatre. The house was so comfortable with plenty of gathering areas for us to enjoy a beverage and the company of good friends. Thanks, Caleb! You couldn't have been more accommodating.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
A beautiful stylish home with great artwork, and a very well equipped kitchen. Perfect spot for our group.
Stayed 4 nights in Feb 2026
Verified review

6/10 Okay

Liked: Check-in, communication, location
Wonderful, communicative host. Beautiful piece of property but a little tired and the pool is in a beautiful setting but deck was overrun with weeds. Also, adding some porch furniture on the deck off the kitchen would be a nice addition. Overall, the house accommodated our family well.
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home is beautiful and functional for a large group. The bedrooms are good sized and comfortable. The kitchen is well equipped and there are plenty of hangout spaces. We loved our stay and were very grateful to have our dogs there.
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
One of a kind house with the friendliest most helpful host this side of the Mississippi. I’ve stayed there twice already with big groups and will definitely be coming back.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dream weekend upstate!!

I cannot recommend this stay enough! The house exceeded our expectations, the host was so helpful and kind, and the proximity to town and Hudson was perfect. We had the best time and cannot wait to come back!
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay!

We had a large group of friends gathering from all over New England and this was the perfect spot! There were plenty of sleeping areas, there were many places to spread out into separate groups, the yard was delightful and the host was very helpful throughout. Highly recommend!!!
Stayed 2 nights in Apr 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

Birkshires 2024

We had a great time.
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend getaway!!!!!!

House is gigantic, pool is amazing and the yard is HUGE. Everything was clean and organized. Host is great with communication both with the property information and places to visit around the area. Will definitely be back soon!!!!!
Stayed 3 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for a group of friends!

This was the perfect place to stay with a group of 11! The house is quite large, has comfortable beds, and an incredible pool. Excellent kitchen for a rental as well — usually when a place says “chefs kitchen” they mean a dull knife and a non-stick pan, but this was actually a fully-stocked kitchen with plenty to space to cook. Would highly recommend to a large group of friends or family!
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Simply fabulous. We loved it! From the info in advance of our stay, to the cleanliness, to the gourmet-ready kitchen, to the charming old house with great AC, to the whimsy artwork. Thank you Caleb!
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, comfortable home

Clean, comfortable, spacious. Tastefully restored house originally built in the 1850s. High ceilings, Plenty of space for hanging out as a group or relaxing separately. High quality furniture and linens. Extra comfy beds! Large, clean swimming pool and tons of nice outdoor space to enjoy.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were a large group of friends and the house
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family of eleven--from 4 to 83--had a wonderful stay at Caleb's property. He is a great host. He made everything very easy and responded right away to questions. The house is spacious, clean, comfortable, and nicely decorated. The grounds gave the kids plenty of space to run and play. They enjoyed exploring the stream and hanging out in the pool. What made the house especially good for our three-generation group was that it is ample. In addition to comfortable bedrooms, there are several sitting areas. The kitchen has plenty of space to cook and eat, and it is stocked with enough dishes, silverware, glasses, and utensils. The pool has enough lounges, and there are lots of pool towels. The game room has puzzles and games for a range of ages. We could have used another bathroom, but we made it work. We enjoyed the beautiful, lively area around Chatham and appreciated Caleb's suggestions. And we recommend Dan's Diner just down the road, It was a great week. Thanks, Caleb!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Upstate NY

Interesting old house with great original art. Beautiful property. Caleb is a nice guy,
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely property with lots to do in the area

Our large family with 8 adults and 6 children enjoyed the distinctive historical house, the pool, the stream, the local theater, restaurants, small towns, local historical sites, Tanglewood, and Art Omi. We had a full six days. The owner is VERY responsive, by the way.
Stayed 5 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing trip!

We had the best weekend at this house. Caleb was wonderful and incredibly responsive. We came with another family and our young children. The house was so accommodating and comfortable. Perfect for a winter weekend and hope to come back to enjoy it again in the summer. Highly recommend!
Stayed 3 nights in Feb 2023
Response from VrboOwner on 26 Feb 2023
Thankyou Ashley. You were wonderful renters. More than welcome back anytime. Take good care. Caleb
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House and property are charming and beautiful. Great collections of books and interesting art. Our host was just delightful. He dealt with a small issue immediately so it was a total non-issue. Location is great…. About 20 min to all sorts of interesting places. Don’t hesitate.
Stayed 14 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Location

Spectacular spacious property for our large, active family. House was wonderfully appointed with everything you need and lots of room for everyone. The pool and patio area made the weekend feel like a resort stay. Caleb could not have been more helpful and was one step ahead of everything we needed. Thank you!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

PERFECTION !

The home was better than we expected - immaculate , spacious and very comfortable. We held our Thanksgiving dinner and we were all delighted by the fully equipped kitchen , game room and overall ambiance ! Caleb was attentive and quick to respond to any questions we had. We will be back !
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

loved every minute

The house and yard are simply perfect for a group of friends looking for a space to reconnect, laugh and enjoy the pool, yard and nature at its best. Some rain, some welcome sun and a shooting star at night while we enjoyed the fire pit. Caleb is a dream host and made us feel welcome. Everything we needed was provided. Thanks Caleb and we hope to return.
Stayed 2 nights in Jul 2023
Response from VrboOwner on 17 Jul 2023
Thankyou Jill. Welcome back anytime. Take good care.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing spot for a group

We absolutely loved our stay at Caleb's house! The property is even prettier than pictured. Everything is super well-kept, from the furnishings to the outdoor grounds. The tasteful decor and gorgeous lawns were a feast for the eyes. We appreciated that the house was super well-stocked with tons of games, extra towels/blankets, and random useful things like lighters, cocktail shakers, etc. Caleb is friendly, communicative, and has great local recs. Several members of my group said they want to come back to the house in the future. Definitely recommend!
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house for a group with beautiful grounds

A group of friends with our kids stayed here over new year’s. Really great house with a good layout, plenty of comfortable beds, on 10 acres with a creek. Well stocked in terms of kitchen as well as sheets, towels, etc. Amazing art all over the house. Beautifully decorated but not stuffy. Super comfortable and cozy. Might be the best rental we’ve ever done! We would love to come back and see the property in all its glory in the summer!
Stayed 2 nights in Dec 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Columbia County

My family and I had a wonderful time at Caleb property, this property is beautiful with a wonderful outdoor area to enjoy with your love one and friends, also the property was ready with blankets, towels, everything you may need. My family and I love Caleb attention asking how everything was before and while we were at the property, also with the flexibility that we were offer for check in and check out. Overall the property was wonderful and Caleb attention 100% we definitely we recommend to anyone.
Stayed 2 nights in May 2023
Response from VrboOwner on 31 May 2023
Thankyou Zugeidy, your family were ideal guests. Welcome back anytime. Take good care. Caleb
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