
Condo vacation rentals in Chatham
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Top-rated condo rentals in Chatham
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chatham condo rentals
Weekly condo rentals

Luxury Apt in Downtown Great Barrington

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

Luxury Ski in Ski out Condo + Amenities

Downtown Albany Large 2BR | Free Parking

Hunter Mountain Ski Retreat - Steps to Lift!

Ski-in/Ski-Out on Jiminy Peak

Slopeside Condo with wood fireplace

“Slopeside at Hunter Mountain”
Pet-friendly condo rentals

Catskills Rustic Chic 4 Bdrm w/ Wood Stove

Meadow View

Luxury 3-bedroom Condo on Windham mountain

Hunter Mountain 2BR Condo - Steps to Slopes!

2. Beautiful, Cozy Condo with view of Windham Mtn

Hiking, fishing,mountain view condo

Cozy Getaway Gem for 2 at Windham Quads.

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite
Condo rentals with a pool

Cozy Gem with Mountain Views

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Hunter & Windham: Hikes, Lakes, Swimming, 2BR

Jiminy Peak Country Inn 1 Bedroom Suite

Wyndham Bentley Brook

Jiminy Peak Country Inn - ski in/out condo MT view
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- Hunter Mountain
- Saratoga Race Course
- Belleayre Mountain Ski Center
- Howe Caverns
- John Boyd Thacher State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Zoom Flume
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Windham Mountain
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bousquet Mountain Ski Area
- Hancock Shaker Village
- Opus 40
- Northern Cross Vineyard
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes