Chatham Holiday Rentals

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Our top choices for Chatham holiday rentals

10.0 out of 10, Exceptional, (9 reviews)
"Loved our stay! Beautiful place and the hosts were very nice. Thank you!"
United States
Kate C.
The price is NZ$616
includes taxes & fees
26 Feb - 27 Feb
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is NZ$524
includes taxes & fees
3 Mar - 4 Mar
Sugar Shack - 300 square feet of pure sweetness.
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 NZ$539
includes taxes & fees
10 Mar - 11 Mar
BLUSH: Boutique TINY home*private spa*walk to town
8.0 out of 10, Very good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is NZ$518
includes taxes & fees
15 Mar - 16 Mar
Renovated house. Built in 1890s. No neighbors in sight.

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (9 reviews)
"Healthy food too!"
United States
GEORGINA
The price is NZ$315
includes taxes & fees
16 Mar - 17 Mar
Huttopia Berkshires
The price is NZ$2,773
includes taxes & fees
1 Mar - 2 Mar
The Catskill and chill Two hours from NYC, Close to Hudson, Kaaterskill falls
9.6 out of 10, Exceptional, (159 reviews)
"The cabin was very clean and cozy"
United States
Azma
The price is NZ$270
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
3.0 star property
8.8 out of 10, Excellent, (2,266 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is NZ$213
includes taxes & fees
26 Feb - 27 Feb
Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is NZ$357
includes taxes & fees
26 Feb - 27 Feb
Charming loft cottage in tranquil Germantown with WiFi, AC

Apartment in South End

2 bed room Apartment
8.8 out of 10, Excellent, (8 reviews)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is NZ$299
includes taxes & fees
1 Mar - 2 Mar
2 bed room Apartment

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (53 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is NZ$222
includes taxes & fees
26 Feb - 27 Feb
All comforts of home

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (137 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is NZ$244
includes taxes & fees
26 Feb - 27 Feb
Micosta Leisure Inn

Holiday Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is NZ$237
includes taxes & fees
26 Feb - 27 Feb
All the comforts of home

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is NZ$558
includes taxes & fees
26 Feb - 27 Feb
Near Tanglewood: Historic Summer Retreat
10.0 out of 10, Exceptional, (13 reviews)
"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"
United States
Abby L.
The price is NZ$307
includes taxes & fees
26 Feb - 27 Feb
Taborton Harvest Boulder Pines Cabin in the woods
3.0 star property
The price is NZ$928
includes taxes & fees
6 Mar - 7 Mar
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Holiday Home in Stottville

Hudson Hot Tub & Pet Escape
The price is NZ$459
includes taxes & fees
26 Feb - 27 Feb
Hudson Hot Tub & Pet Escape
10.0 out of 10, Exceptional, (1 review)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is NZ$307
includes taxes & fees
26 Feb - 27 Feb
Taborton Harvest Timber Trails Unique cabin experience
9.8 out of 10, Exceptional, (35 reviews)
"Cozy and a great front porch to enjoy morning coffee and the evenings."
United States
Crystal B.
The price is NZ$559
includes taxes & fees
1 Mar - 2 Mar
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.6 out of 10, Exceptional, (30 reviews)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
United States
Maura S.
The price is NZ$391
includes taxes & fees
3 Mar - 4 Mar
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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

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 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 NZ$213 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?

Pool & Secluded Historic Estate on the Hudson | River House by AvantStay: This holiday home rental outside of Chatham is located on a river, and has an arcade/games room, a BBQ and air conditioning to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chatham?

With 14 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 Kinderhook Lake. The Mac-Haydn Theatre and Van Alen House 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.