Chatham Holiday Rentals

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Holiday Rentals in Chatham

Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is HK$1,319
HK$1,525 total
includes taxes & fees
4 May - 5 May
Vacation Village in the Berkshires
Private kitchen
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is HK$1,164
HK$1,277 total
includes taxes & fees
8 May - 9 May
Jiminy Peak Mountain Resort
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, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Balcony
Micosta Leisure Inn
3.0 star property
8.8 out of 10, Excellent, (70)
"Very nice. "
The price is HK$980
HK$1,101 total
includes taxes & fees
8 May - 9 May
Micosta Leisure Inn
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!!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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
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 HK$1,164
HK$1,449 total
includes taxes & fees
8 May - 9 May
Mountainside Condo Ski In Ski Out
View from property
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (96)
"Loved the lake house!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Outdoor dining
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Beautiful, Private Estate w/ Pool, Pond, Rec Room, Gym, Library, Barn, Trails!
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, Private Estate w/ Pool, Pond, Rec Room, Gym, Library, Barn, Trails!
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
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!
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!
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
Near Tanglewood: Historic Summer Retreat
9.0 out of 10, Wonderful, (6)
"Clean and comfortable house with lots of character 15 minutes away from Jimini Peak. Watch your head on the stairs and beware of a few ladybugs. Family of 5 had a great weekend hiking, skiing, eating and drinking. Would rent again."
The price is HK$977
HK$2,524 total
includes taxes & fees
9 May - 10 May
Near Tanglewood: Historic Summer Retreat
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
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The Winthrop Estate - 12K SF 32 Acres
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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.

Other types of properties in Chatham you may be interested in

Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (232)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot "
The price is HK$774
HK$864 total
includes taxes & fees
9 May - 10 May
Life House Berkshires
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (872)
"A great inn. "
The price is HK$922
HK$1,205 total
includes taxes & fees
6 May - 7 May
The Red Lion Inn
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Our room was on the lake and had a nice deck where we could relax with a beer purchased (very cheap!) from the front reception area. Also the Indian restaurant was excellent with ample portions. And because it's in MA, everything was ADA accessible which made it feel inclusive to all. Some guest had their dogs with them but the place was very clean even with pets. "
The price is HK$790
HK$883 total
includes taxes & fees
9 May - 10 May
The Black Swan Lee - Lenox, Ascend Hotel 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.

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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?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Chatham is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chatham?

With 18 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 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.

Recent reviews of Chatham properties
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Our room was on the lake and had a nice deck where we could relax with a beer purchased (very cheap!) from the front reception area. Also the Indian restaurant was excellent with ample portions. And because it's in MA, everything was ADA accessible which made it feel inclusive to all. Some guest had their dogs with them but the place was very clean even with pets. "
A verified traveller stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 10 hours ago
The Black Swan Lee - Lenox, Ascend Hotel Collection