Chatham Holiday Rentals

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Holiday Rentals in Chatham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1978)
"Beautiful location!"
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (65)
"Really beautiful place to enjoy nature with family!!"
The price is AU$287
includes taxes & fees
1 Sept - 2 Sept
Postcard Cabins Eastern Catskills

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (969)
"Quiet, clean, accessible. "
The price is AU$272
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
The price is AU$223
includes taxes & fees
1 Sept - 2 Sept
Micosta Leisure Inn

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is AU$167
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (127)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (27)
"Great location "
The price is AU$520
includes taxes & fees
7 Sept - 8 Sept
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is AU$295
includes taxes & fees
1 Sept - 2 Sept
Taborton Harvest Boulder Pines Cabin in the woods

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Charming Yacht on Catskill Creek

9.8 out of 10, Exceptional, (8)
"Melisa, the owner, couldn't have made more pleasant and been more available. Without be intrusive. Can only add " if your looking for a different experience. This is it" "
The price is AU$343
includes taxes & fees
8 Sept - 9 Sept
Charming Yacht on Catskill Creek

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,334
includes taxes & fees
5 Sept - 6 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (29)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is AU$1,623
includes taxes & fees
2 Sept - 3 Sept
Hancock Village Inn at Jiminy Peak

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"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."
The price is AU$283
includes taxes & fees
1 Sept - 2 Sept
Taborton Harvest Timber Trails Unique cabin experience

Private Yacht on Catskill Creek

9.8 out of 10, Exceptional, (26)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is AU$380
includes taxes & fees
2 Sept - 3 Sept
Private Yacht on Catskill Creek

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$733
includes taxes & fees
29 Sept - 30 Sept
Comfortable Berkshires retreat on mtn resort, SISO

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (166)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Rose Cottage

9.0 out of 10, Wonderful, (7)
"It's so peaceful there. It was lovely."
Rose Cottage

Charming Catskill getaway walking distance to Main St. Pet-friendly!

10.0 out of 10, Exceptional, (6)
"We had a 2 night stay while in Catskill for a wedding. My hubby, 8 year old and 2 dogs in tow. House was just right for us. My son loved the board games available and the foosball table. House is uncluttered and very clean. Surrounding are is historic with a short walk to downtown shops. I would definitely rent here again. "
Charming Catskill getaway walking distance to Main St. Pet-friendly!
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

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$167 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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This holiday home rental outside of Chatham is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chatham?

With 12 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.