Search Vacation Homes in Chatham

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Vacation Homes in Chatham

Our top choices for Chatham vacation homes

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

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

9.8 out of 10, Exceptional, (146)
"This house was amazing more than expected, I love it, my family had a great time in there. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (37)
"House was perfect! Great location and beautiful home. Hosts were very helpful and everything was perfect!"
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (72)
"Nice place in a convenient location."
Enjoy comfortable elegance in this secluded grand home located in town
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (30)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (48)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
General Williams Estate House Lenox/Stockbridge
Exterior

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"Enjoyed our stay for a girls weekend. Big house, well kept up, with nice bedrooms and bathrooms, lots of places for us to hang out. Close to lots of things in the berkshires. Would definitely stay again."
General Williams Estate House Lenox/Stockbridge
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (25)
"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Outdoor spa tub

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (54)
"Modern and extremely clean. Every amenity worked and was in great shape. We used the fire pit, grill, kayaks, canoe, and hot tub without any problems. Well stocked kitchen with place settings and extra spices etc. Super easy check-in. And host quickly responded to any questions. Everything was perfect!"
The price is SAR 1,126
SAR 2,147 total
includes taxes & fees
8 Oct - 9 Oct
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is SAR 2,060
SAR 3,930 total
includes taxes & fees
10 Sep - 11 Sep
Hancock Village Inn at Jiminy Peak
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is SAR 1,097
SAR 2,307 total
includes taxes & fees
16 Sep - 17 Sep
Spacious 5-bedroom house in charming Lee with WiFi
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is SAR 604
SAR 1,781 total
includes taxes & fees
10 Sep - 11 Sep
Comfortable Berkshires retreat on mtn resort, SISO
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Interior

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.0 out of 10, Wonderful, (17)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (7)
"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!
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Great house. More then Enough room for two families. Clean and as described. Super close to butternut ski mountain. "
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
2 bedroom town house with game room
Fridge, microwave, oven, stovetop

2 bedroom town house with game room

5.8 out of 10, (16)
"We didn’t stay. "
2 bedroom town house with game room
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Catskill Cottage Walk to Downtown & River Views
Interior

Catskill Cottage Walk to Downtown & River Views

10.0 out of 10, Exceptional, (10)
"We rented the cottage "
Catskill Cottage Walk to Downtown & River Views
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Great"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge Village Cottage With Mountain View’s and walk to town
Outdoor dining

Stockbridge Village Cottage With Mountain View’s and walk to town

9.8 out of 10, Exceptional, (63)
"Perfect long weekend with family at this lovely home!"
Stockbridge Village Cottage With Mountain View’s and walk to town
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

10/10 Excellent
"Hotel was immaculate! Our room was in beautiful condition, fully stocked with perfectly cleaned bedding, towels etc. We appreciated the hot breakfast in the morning, given the relatively small space it was a great selection and the food was tasty. I like that a pool was available; even though I didn't have time to use it it's nice to know. Finally, the staff I interacted with were quite friendly and welcoming, though I didn't get names. We checked in on Thursday evening at about 8 PM and checked out at about 9:30 on Friday morning; both of the front desk employees I spoke with were great. Thank you so much for an easy and comfortable stay during a difficult time."
James 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very enjoyable stay in a beautiful location! Clean, comfy, and nicely decorated condo! The staff is so helpful, and absolutely amazing. Couldn’t have had a better place to stay!"
Sandra 6-night trip
Posted 7 days ago
Vacation Village in the Berkshires

Explore a world of travel with Expedia

Explore a world of travel with Expedia