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Holiday Homes in Chatham

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chatham holiday homes

Property grounds

1. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AU$561
includes taxes & fees
23 Aug - 24 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

2. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is AU$796
includes taxes & fees
14 Sept - 15 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

3. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AU$203
includes taxes & fees
24 Aug - 25 Aug
All the comforts of home
Coffee/tea maker, fridge, microwave, oven

4. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AU$333
includes taxes & fees
19 Aug - 20 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
TV, DVD player, books, video library

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AU$341
includes taxes & fees
9 Sept - 10 Sept
1800s Carriage house in Berkshires / Hudson Valley
TV, fireplace, DVD player, books

6. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is AU$1,076
includes taxes & fees
21 Aug - 22 Aug
Mtn-View Retreat in Huson Valley: Great for Groups
Interior

7. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (25 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
The price is AU$285
includes taxes & fees
24 Aug - 25 Aug
Catskill Cottage Walk to Downtown & River Views
Pool

8. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is AU$1,024
includes taxes & fees
19 Aug - 20 Aug
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Terrace/patio

9. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
Athens
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful property that was clean. Hosts left information about surrounding area and restaurants- we definitely felt welcomed when we arrived. Beautiful area with lots to do! Would stay here again"
United States
Sarah M.
The price is AU$851
includes taxes & fees
19 Aug - 20 Aug
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Exterior

10. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AU$752
includes taxes & fees
8 Sept - 9 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Interior

11. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$457
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Outdoor dining

12. Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
10.0 out of 10, Exceptional, (1 review)
"We were only there for one night, but we really liked this space - it was clean and the beds were so comfortable! Thanks so much to our host for opening his home to us."
United States
Rachel P.
The price is AU$492
includes taxes & fees
31 Aug - 1 Sept
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Interior

13. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AU$437
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, oven, stovetop, dishwasher

14. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (1 review)
"Inside the cabin was fantastic! Modern, clean, well stocked with essentials. We very much enjoyed our time in the cabin. The town was so charming and fun to explore. Was not expecting the auto/junk yard atmosphere on the outside. I understand why it wasn’t part of the description of the property. That being said, the neighbors did not bother us during our stay."
United States
Vicki M.
The price is AU$381
includes taxes & fees
17 Aug - 18 Aug
Cozy Catskill Escape
Coffee/tea maker, fridge, microwave, stovetop

15. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$798
includes taxes & fees
16 Aug - 17 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

16. Modern cabin retreat

Modern cabin retreat
Catskill
The price is AU$396
includes taxes & fees
14 Sept - 15 Sept
Modern cabin retreat
Exterior detail

17. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is AU$746
includes taxes & fees
9 Sept - 10 Sept
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Coffee/tea maker, fridge, microwave, oven

18. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is AU$1,120
includes taxes & fees
8 Sept - 9 Sept
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
TV

19. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is AU$431
includes taxes & fees
8 Sept - 9 Sept
Cabin Oasis near Town
Smart TV

20. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$565
includes taxes & fees
24 Aug - 25 Aug
stylish Berkshires Retreat
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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Top Chatham Hotel Reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
Sheila 1-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Lenox

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
169
Accommodation
516 Holiday Homes
Lowest Price
AU$203
Highest Price
AU$1,120