A city street with buildings, parked cars, and solar panels.

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chatham vacation rentals

A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

1. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
The price is ￥42,195
￥53,777 total
includes taxes & fees
Nov 3 - Nov 4
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

2. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is ￥42,195
￥53,777 total
includes taxes & fees
Nov 16 - Nov 17
BLUSH: Boutique TINY home*private spa*walk to town
Exterior

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,374
￥53,587 total
includes taxes & fees
Nov 3 - Nov 4
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern building with a wooden deck and a door.

4. 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, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (192 reviews)
"Great stay"
United States
George
The price is ￥15,546
￥17,412 total
includes taxes & fees
Nov 1 - Nov 2
Micosta Leisure Inn
A wooden deck with a staircase leading to a covered porch area.

6. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is ￥15,389
￥20,748 total
includes taxes & fees
Oct 29 - Oct 30
All comforts of home
Exterior

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,233 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
The price is ￥13,500
￥18,598 total
includes taxes & fees
Nov 22 - Nov 23
Berkshire Mountain Lodge
A wooden deck with a staircase leading to a covered porch area.

8. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ￥16,660
￥22,174 total
includes taxes & fees
Nov 9 - Nov 10
All the comforts of home
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

9. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (329 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is ￥26,511
￥35,408 total
includes taxes & fees
Oct 28 - Oct 29
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

10. 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 ￥10,981
￥32,278 total
includes taxes & fees
Nov 3 - Nov 4
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

11. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,799 reviews)
"We had an amazing stay."
United States
Luke
The price is ￥12,603
￥15,798 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A backyard with a fire pit, wooden deck, and string lights.

12. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is ￥29,335
￥56,925 total
includes taxes & fees
Nov 9 - Nov 10
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A spacious living room with a dining area, a kitchen, and a large window.

13. 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 ￥13,334
￥35,333 total
includes taxes & fees
Nov 5 - Nov 6
1800s Carriage house in Berkshires / Hudson Valley
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

14. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.4 out of 10, Exceptional, (6 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is ￥31,217
￥59,209 total
includes taxes & fees
Oct 29 - Oct 30
Hudson NY’S Country Serenity Guest Suite.
A bedroom with a wooden bed, a window with a view of trees, and a red chair.

15. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window. The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail. The common area had everything we needed, clean, comfortable. If you want to relax, this is pretty special!"
United States
Trena
The price is ￥19,766
￥28,905 total
includes taxes & fees
Oct 29 - Oct 30
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

16. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is ￥15,530
￥23,480 total
includes taxes & fees
Nov 3 - Nov 4
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

17. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is ￥14,725
￥36,673 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires Apartment at the Stephentown Hotel
A rustic cabin interior with a stone wall, wooden furniture, and a cozy seating area.

18. Magic Forest Farm's Enchanted Cabin

Magic Forest Farm's Enchanted Cabin
Coeymans Hollow
9.6 out of 10, Exceptional, (19 reviews)
"Cool and unique spot. Great host!"
United States
Andrew S.
The price is ￥10,856
￥15,127 total
includes taxes & fees
Oct 28 - Oct 29
Magic Forest Farm's Enchanted Cabin
A spacious kitchen with wooden cabinets, a large island, and a dining area with benches.

19. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (7 reviews)
"It was a great getaway "
United States
Chandra F.
The price is ￥17,648
￥26,555 total
includes taxes & fees
Oct 29 - Oct 30
Taborton Harvest Timber Trails Unique cabin experience
A cabin with a triangular window, wooden walls, and a bed with pillows.

20. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is ￥41,425
￥44,739 total
includes taxes & fees
Nov 27 - Nov 28
Gather Greene
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

Hotel On North

Hotel On North

10/10 Excellent
"Very large room and bathroom. Had parking easily accessible, very nice and helpful staff."
Gaby 2-night trip
Posted 5 hours ago
Hotel On North

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
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  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chatham?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.