Chatham Holiday Rentals from AU$143: Search Short-Term Rentals

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

Catskill Cottage Walk to Downtown & River Views : This holiday home rental outside of 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 holiday 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

Lori S.

includes taxes & fees

2 Nov - 3 Nov

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

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

Chatham

Jess S.

includes taxes & fees

15 Nov - 16 Nov

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

3. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

includes taxes & fees

16 Nov - 17 Nov

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

4. Micosta Leisure Inn

Hudson

George

includes taxes & fees

1 Nov - 2 Nov

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

5. All comforts of home

Hudson

Douglas

includes taxes & fees

27 Oct - 28 Oct

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

6. Berkshire Mountain Lodge

Pittsfield

Joel

includes taxes & fees

22 Nov - 23 Nov

7. All the comforts of home

Hudson

Lori M.

includes taxes & fees

4 Nov - 5 Nov

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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

Catskill

Darryl

includes taxes & fees

23 Nov - 24 Nov

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Top Chatham Hotel Reviews

Berkshires Untold

10/10 Excellent

"Berkshires Untold is THE PLACE to stay in Lenox. The rooms are terrific. They've been beautifully upgraded and the bathrooms are big and as nice as can be. We were concerned about the noise from the cars on Rte 7 as our room faced the street, but it was not an issue whatsoever. The breakfasts were just right. Coffee was plentiful and ready in the morning when we got up. And the owners (or managers) are suburb; they handled a problem I had with such grace and so generously I was astounded! Bottom line: next time we return for a Foliage experience, we're coming back to the Berkshires Untold!"

The Yankee Inn

10/10 Excellent

"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."

Find out more about Chatham

Everything you need to know about Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Chatham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham holiday rentals we have selected for you start as low as AU$143 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing stay. Chatham is known for its theatres and restaurants.

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

Catskill Cottage Walk to Downtown & River Views: This holiday home rental outside of 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 holiday rentals are there in Chatham?

With 11 Expedia holiday rentals, you're guaranteed 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 wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.

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Check prices for these dates

Our top choices for Chatham holiday rentals

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

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