Chatham Vacation Rentals

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Vacation Rentals in Chatham

7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
View from property
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (97)
"Lovely chalet by the lake, we had such a relaxing stay. The place is just like on the pictures, very quiet but not far from amenities. The host are very friendly super responsive. Thanks for having us!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
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Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"We had a wonderful time at the Moose Lodge. It was perfect for our family. Very clean, everything we needed and the property managers were extremely communicative. Thank you!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Fridge, microwave, oven, stovetop
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (126)
"Great time, beautiful property, host very responsive and helpful. Awesome sound system bring your CDs."
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (79)
"There were 6 adults and 2 infants in our party, we were in town for our 25 year high school reunion. The house was incredible and the host went above and beyond to make sure we were well taken care of. This place is a hidden gem and deserves all of the praise."
Antique Farmhouse Totally Restored
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Shower, hair dryer, towels
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (10)
"The number of bedrooms and bathrooms was great for the 13 of us. The big kitchen, pantry and long dining tables made for fun interaction. The game room with pool table and ping pong table were perfect for after dinner fun. Beautiful property on the river. We plan to go back. Historic homes are tough to maintain and our hope is that it is as nice in the future as it was this week."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Exterior
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is CA $217
CA $446 total
includes taxes & fees
May 27 - May 28
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Fridge, microwave, oven, stovetop
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, (79)
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
Interior
River Lodge by AvantStay | 11 BR Historic Estate w/ Pool & Views of Hudson!
9.6 out of 10, Exceptional, (8)
"River Lodge is perfect for our big family. We stayed for a long weekend. The house is spacious with lots of things to do. Outdoor space is huge with a beautiful view of the Hudson River. Highly recommend!"
River Lodge by AvantStay | 11 BR Historic Estate w/ Pool & Views of Hudson!
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (72)
"Expedia said they have a Sunday buffet, but they didn't."
The price is CA $171
CA $192 total
includes taxes & fees
May 26 - May 27
Micosta Leisure Inn
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Pool
Mountainside Condo Ski In Ski Out
8.8 out of 10, Excellent, (8)
"Great location and nice unit. Had a blast!"
The price is CA $203
CA $254 total
includes taxes & fees
May 28 - May 29
Mountainside Condo Ski In Ski Out
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Don't see what you're looking for?
See all available properties in Chatham
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.

Chatham Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Chatham private vacation homes
Known landmarks
The Mac-Haydn Theatre, Hudson Chatham Winery and Shaker Museum and Library
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Chatham you may be interested in

Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (243)
"Love the lobby (even smells great!) Love the decor and the outdoor patio. Happy with entire stay."
The price is CA $135
CA $151 total
includes taxes & fees
May 28 - May 29
Life House Berkshires
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (885)
"Stay was great"
The price is CA $195
CA $249 total
includes taxes & fees
May 27 - May 28
The Red Lion Inn
Front of property
The Lenox Collection
3.5 star property
8.8 out of 10, Excellent, (207)
"😊"
The price is CA $133
CA $148 total
includes taxes & fees
May 27 - May 28
The Lenox Collection
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.

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chatham vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham vacation rentals we have selected for you start as low as CA $171 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 vacation 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 vacation.

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 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?

Fox Hollow Luxury Ranch Laurel Lake: This vacation home near Chatham is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Chatham?

With 17 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.

Recent reviews of Chatham properties
Expedia verified reviews

The Lenox Collection

The Lenox Collection

5/5 Excellent
"😊"
A verified traveller stayed at The Lenox Collection
Posted 1 day ago
The Lenox Collection