
Condo vacation rentals in Chatham
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Top-rated condo rentals in Chatham
Guests agree: these condos are highly rated for location, cleanliness, and more.

2BR w/ Parking + deck - Near Downtown & MVP Arena
Bright, peaceful 2BR unit set just outside Albany’s vibrant Center Square within walking distance to Washington Park, local cafés, restaurants, and downtown attractions. Whether you’re a solo traveler, couple, or family, you’ll find everything you need for a relaxing stay. Sip your morning coffee on the private deck with birdsong in the background, rest in a cozy queen or full bed, and enjoy self check-in, fast Wi-Fi, climate control with A/C and heat, and private garage parking right next door.
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Stunning Views • Bright 2BR • Pool • Near Farm • Lakes • Farm
A quiet mountain hideaway where the air feels soft and clean, and the view from the deck slows your whole spirit down. This cozy 2BR retreat sits between Windham and Hunter—perfect for families, solo wanderers, and anyone craving calm. Fast WiFi, a full kitchen, and short stays on selected days make it easy to escape, breathe, rest, and reconnect with yourself. Easy drive to charming little towns - Windham, Hunter , Tannersville . Swimming pool on premises , CD Lane Lake with beach and free boat
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Hunter Mtn. Clean Cozy Close Condo *Great Reviews*
Village of Hunter clean, cozy studio condo featuring vintage decor. Short walk to Ski Slopes, Snowtubing, Scenic Skyride, Dolan's Lake/Beach, Pickle Ball & Basketball Courts, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. Murphy bed w/ full size comfy Casper Mattress, sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks
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walking distance to town and waterfront
Perfect for friends, couples, families, or solo-travelers looking for a comfortable home that’s centrally located and near some of Kingston’s best restaurants and shops! This historic two-unit home is walking distance to the waterfront and a short drive to incredible hikes and farms! *Pet-friendly (no extra fee) *Family-friendly (highchair + Pack n Play for babies, games for kids). Note: Parking onsite or arrive via Metro North to Poughkeepsie, Amtrak to Rhinebeck, or bus to Kingston
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Hike Minnewaska + Walk to Rail Trail, Food, Drink
Your home base in the Kerhonkson/Accord area - walk to the O&W rail trail, Mill + Main, and Flying Goose or drive 10 mins to Minnewaska, Mohonk, and other great dining options. This sunny 3 BR, 2 BA apartment feels like a full home: private deck, fenced yard, dreamy beds, and loads of local art. You'll find custom Two Queens coffee, great games, a stocked kitchen, and fun design touches throughout. Dog-friendly, fully equipped, and in a perfect spot to explore the best of the Catskills
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Cozy Slope Side Retreat
Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.
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Windham Condo
This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills. The complex has a pool, tennis, pickleball & basketball courts and a fire pit. Enjoy the mountain air while working from home with dedicated Wifi. We have a well-stocked kitchen, wood-burning fireplace, and comfy deck. Your place to enjoy all the hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.
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Cozy Gem with Mountain Views
A cozy apartment located less than a mile away from premier skiing and snowboarding at Hunter Mountain. Our place is located in a lovely community that has plenty of space to enjoy some quality time with family and friends. This is our home away from home and you can experience lot of personal touches throughout the apartment such as custom wood work, family photos and seasonal decoration. We can not wait for you to enjoy the beauty of Catskill mountains.
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Liftside Hunter Mtn. Best Ski On/Off 2BR/2BA.
Immaculate liftside location, located in the coveted Liftside Village at the base of Hunter Mountain. This is a family and friends ski and hiking paradise. Experience all the comfort and beauty you could ask for in the very best location. Walk to ski slopes, tubing, hiking trails, base lodge and Van Winkles Restaurant. Cable, Wifi, Xbox, games, fully equipped kitchen with coffee bar and every amenity. Ask about seasonal summer rentals.
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Elegant, spacious studio apt in historic mansion
Welcome to the Plaza Suite, a newly renovated studio condo in an historic Center Square mansion. Enter through a grand reception hall/art gallery and climb the oak staircase to the sunny and spacious second floor apartment. There's a nice view of State Street and the Empire State Plaza. Features include: a new fully equipped kitchen, comfy lounge area, dining /work table, renovated vintage bathroom, walk-in closet and new queen bed.
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Cozy Downtown Hunter Mountain Getaway
Keep it simple at my peaceful and centrally-located loft. You are at the footsteps of Hunter Mountain, right beside Dolan's Lake and a very short drive to all of Village of Hunter restaurants, bars, cafes, hikes and conveniences. You can easily walk to Hunter Mountain and the Trailways Bus line. The condo has its own wifi and 2 roku TV’s.
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Downtown Adams Vintage Getaway
Your family will be close to everything when you stay at this centrally-located place. Walk to the Adams Theater, rail trail, grocery store, restaurants, shops, or take a quick drive to MassMoCA, Jiminy Peak, or Greylock Glen. This is the perfect location for all north county has to offer. One free parking spot in back of building.
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Popular amenities for Chatham condo rentals
Weekly condo rentals

Quiet/cozy, close to slopes apartment
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Luxury Apt in Downtown Great Barrington
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Hunter Mountain Condo | Walk to Lifts & Town
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the NAMA nest
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WindhamWay MainSTREET Retreat*5 min to the Slopes
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Peaceful Windham Townhome - Only 8 mi from Hunter!
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Trailside Tranquility at Hunter Mountain
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Ski ON/OFF - Brand New Renovated Unit - Hunter, NY
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Pet-friendly condo rentals

Catskills Rustic Chic 4 Bdrm w/ Wood Stove
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Slope Side Luxe | Views, Decks, Walk to Mtn & Town
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Hideaway Windham/Hunter Fireplace, Snow & Skiing
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Meadow View
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Historic Gem, Fireplace,2BR/2BA,Capitol District
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Hunter Mountain 2BR Condo - Steps to Ski Slopes!
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Snowboarding skiing Mountain View condo
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Cozy Getaway Gem for 2 at Windham Quads.
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Condo rentals with a pool

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub
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Berkshires Vacation Village
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Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
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Windham Mountain Ski In Ski Out - Pool Hot Tub Gym
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Luxury Ski in Ski out Condo + Amenities
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THE SLOPE slope-view Country Inn 1BR w/heated pool
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Jiminy Peak Apartment
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Jiminy Peak Country Inn 1 Bedroom Suite
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Destinations to explore
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- Mont-Tremblant Vacation rentals
- Hunter Mountain
- Belleayre Mountain Ski Center
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- June Farms
- Catamount Mountain Ski Resort
- Howe Caverns
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Thacher State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Millbrook Vineyards & Winery
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- Saratoga Spa State Park
- MVP Arena
- Naumkeag
- New York State Museum





