Chatham Holiday Rentals from €90: 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 deck with a lattice railing, surrounded by lush greenery and a gravel path.

1. Micosta Leisure Inn

Hudson

Kim

includes taxes & fees

27 Oct - 28 Oct

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

2. Berkshire Mountain Lodge

Pittsfield

Kathleen

includes taxes & fees

9 Nov - 10 Nov

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Williamstown

Pofen

includes taxes & fees

11 Nov - 12 Nov

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

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

Catskill

Darryl

includes taxes & fees

11 Nov - 12 Nov

A cabin with a triangular window, wooden walls, and a bed with pillows.

5. Gather Greene

Coxsackie

Jabari

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

includes taxes & fees

14 Oct - 15 Oct

A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

7. Gatherwild Ranch

Germantown

includes taxes & fees

14 Oct - 15 Oct

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Top Chatham Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Amazing pool and great full kitchens in rooms."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

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, apart-hotels, 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 favorite 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 depends 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 €90 per night. Entering your travel dates in the search wizard you might find 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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