Entire home

Gorgeous large renovated historic home on 10 acres with pool

Family-friendly holiday home in Chatham with an outdoor pool

Overview
Amenities
Policies
Location

Exceptional

5 bedrooms2+ bathroomsSleeps 144000 sq ft

Popular amenities

Pet-friendly
Parking available
Dryer
Washer
Fireplace

Explore the area

Chatham, NY

Place, The Mac-Haydn Theatre
‪8 min drive‬
Place, National Shrine of the Divine Mercy
‪25 min drive‬
Place, Tanglewood Music Center
‪30 min drive‬
Airport, Hudson, NY (HCC-Columbia County)
‪22 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

About this property

Gorgeous large renovated historic home on 10 acres with pool

Built it 1850, this incredible home is one the loveliest in the area. Recently fully restored and updated, our 5 bedroom home with living room, formal dining room, den, library, and eat-in chefs kitchen is fully equipped with everything you would need to host up to 14 people, and many more on extra mattresses to be provided if needed. With 10 Acres, an enormous pool and fabulous gardens and fields, this house is set up for you and your family and friends to enjoy a country escape.

Add dates for prices

Amenities

Pool

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

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Pool
Kitchen
Washer
Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 24

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 3 total)

Please keep pets off furniture

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:

Start the dishwasher

Strip any used beds and gather used towels

Take out the rubbish

Turn off the lights

Please strip all beds and leave all dirty sheets/towels/bathmats by the washer/dryer in the kitchen

Please throw all rubbish and recycling tin the bins on stever hill and make sure the bin straps are on tightly

Failure to complete these may result in a negative review from the host.

Please keep pets off furniture

Please use plastic cups in the pool area. They are located in the upper left cabinet next to the kitchen sink.

Please keep the bungee cords tightly on the trash and recycling bins otherwise animals will make a mess.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Long-term renters welcome

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

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. Travelling with kids? Consider Ebenezer II Gifts and Antiques and Hotchkiss Mobile Studio. Explore all the area has to offer with hiking and cycling.

View more Holiday homes in Chatham

Chatham, NY

What's nearby

The Mac-Haydn Theatre - 8 min drive - 8.5 km
Norman Rockwell Museum - 24 min drive - 29.9 km
National Shrine of the Divine Mercy - 25 min drive - 32.1 km
Catamount Ski Area - 29 min drive - 35.8 km
Tanglewood Music Center - 30 min drive - 36.6 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
‪Bartlett House - ‬7 min drive
‪Chatham Chinese Restaurant - ‬6 min drive
‪Yiannis - ‬6 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).

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, Art Omi International Arts Center - Fields Sculpture Park and Omi International Arts Center. Ebenezer II Gifts and Antiques and Hotchkiss Mobile Studio are also within 12 miles (20 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

10/10 Excellent

Eva J.

30 Aug, 2025

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

10/10 Excellent

Kelsey M.

3 Sept, 2025

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

We were a large group of friends and the house

Stayed 2 nights in Jul 2025

10/10 Excellent

Peter L.

6 Aug, 2025

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

10/10 Excellent

Verified traveller

25 Aug, 2025

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

10/10 Excellent

Ethan T.

6 Jul, 2025

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

8/10 Good

Luke S.

4 Jul, 2024

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

Birkshires 2024

We had a great time.

Stayed 4 nights in Jun 2024

10/10 Excellent

Maria C.

9 Jun, 2024

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

10/10 Excellent

Sue L.

30 May, 2025

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

10/10 Excellent

Bruce K.

16 Sept, 2024

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

10/10 Excellent

Tracy W.

2 Dec, 2024

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

10/10 Excellent

chris w.

17 Jun, 2024

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

10/10 Excellent

Samantha R.

15 May, 2024

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

10/10 Excellent

Dawn O.

13 Aug, 2024

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

10/10 Excellent

Joyce T.

7 Jul, 2024

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

10/10 Excellent

Ashley P., Brooklyn

26 Feb, 2023

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

10/10 Excellent

ZUGEIDY N.

31 May, 2023

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

10/10 Excellent

Lindsay C., Brooklyn

1 Jan, 2024

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

10/10 Excellent

Jill M., Massachusetts

17 Jul, 2023

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

10/10 Excellent

Conor M.

12 Jun, 2023

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

Simply the best

It is hard to explain how wonderful this house is and how gracious and thoughtful a host Caleb is, but I'll try briefly. The check in process was seamless, everything we needed was there, he even helped with local recommendations. The house itself is spacious, well designed and full of character and art. There were 12 of us and this house provided plenty of communal areas (amazing yard) as well as comfortable nooks to have a serene up state moment to yourself. Caleb was responsive and communicative leading up to, throughout, and after the stay. 10 out of 10 upstate getaway, five stars, would recommend, will be back.

Stayed 3 nights in Jun 2023

10/10 Excellent

Stewart D.

11 Aug, 2024

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

Our home away from home!

Very comfortable historic home with its own private park in the backyard. We stayed eight nights with eleven people and had a grand time. Super clean and well furnisher. We cooked in four nights and ate out four nights. The kitchen is big enough for two or three people cooking and prepping and the dining room was fine for all eleven of us to enjoy dinner together. Very cozy kid space upstairs. Multiple living rooms let various people do their thing. Great pool and yard. The owner is super friendly and responsive. He checked in with us every so often to make sure everything was OK. Our family made some great memories during our stay. Highly recommended!

Stayed 8 nights in Jul 2024

10/10 Excellent

Betsy K.

1 Jul, 2024

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

Special house and weekend!!!!

This was the perfect place to gather with family to celebrate our 50th wedding anniversary! The delightful house is sprawling and had multiple areas for us to gather in various configurations including a well stocked playroom. We felt like we were constantly discovering new rooms! Caleb was very responsive and although he offered many suggestions for things to do in the area we didn’t budge from the house all weekend. The enormous yard is gorgeous and the kids (and adults) couldn’t get enough of the pool. Everything we needed was provided including an endless supply of pool towels! We very much appreciated the early check-in. Our family had a wonderful time and have already asked if we can return to celebrate our 51st! Thank you, Caleb!

Stayed 2 nights in Jun 2024

10/10 Excellent

Conor M.

31 Aug, 2025

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