Chatham Vacation Rentals from ￥17,090: Search Short-Term Rentals

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

Catskill Cottage Walk to Downtown & River Views : This vacation home 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.

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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.

Chatham

Sue G.

￥48,926 total

includes taxes & fees

Sep 17 - Sep 18

A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

2. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

￥48,926 total

includes taxes & fees

Sep 17 - Sep 18

A camping setup with a metal chair and a table by a river in a forest.

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

Chatham

Jess S.

￥52,740 total

includes taxes & fees

Sep 20 - Sep 21

A modern building with a wooden deck and a door.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

￥108,073 total

includes taxes & fees

Sep 15 - Sep 16

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. Micosta Leisure Inn

Hudson

Andrea

￥20,312 total

includes taxes & fees

Sep 16 - Sep 17

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

6. Berkshire Mountain Lodge

Pittsfield

Robert

￥17,090 total

includes taxes & fees

Oct 1 - Oct 2

A wooden deck with a staircase leading to a covered porch area.

7. All comforts of home

Hudson

Georgine

￥20,420 total

includes taxes & fees

Sep 14 - Sep 15

8. All the comforts of home

Hudson

Julie B.

￥21,823 total

includes taxes & fees

Sep 14 - Sep 15

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Top Chatham Hotel Reviews

Berkshires Untold

8/10 Good

"I didn’t like that you didn’t have a chair outside your room. It was very dark and confining once you were all the way upstairs with very little ease of access with no elevator to bring you back below, so it would’ve been nice to have some way of being outside without having to go back downstairs."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

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:

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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 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 12 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.

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Check prices for these dates

Our top choices for Chatham vacation rentals

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

2. BLUSH: Boutique TINY homeprivate spawalk to town

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