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Condo vacation rentals in Chatham

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Vacation rentals for every style

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Popular amenities for Chatham condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

A modern living area features a large flat-screen television mounted on a dark green wall. Comfortable seating is provided by a yellow armchair and a blue sofa, draped with a cozy throw. Natural light filters through the windows, with greenery placed tastefully in the corners.
Condo in Albany
New place to stay

Cozy Luxury Brownstone Stay w/ Yard & Parking

The exterior of the resort is highlighted by a wooden gazebo surrounded by lush greenery. The three-story building features gabled roofs and multiple balconies, with warm lights illuminating the windows during twilight.
Condo in Hancock
4.89 out of 5 average rating, 9 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

A cozy living room features a stone fireplace with stacked firewood beside it. Comfortable brown sofas surround a dark wooden coffee table, which holds decorative items. Natural light filters through the window with blinds, illuminating the warm wall color.
Condo in Lanesville
5 out of 5 average rating, 10 reviews

Hunter condo with access to Hunter Mountain

A dining area is filled with natural light, featuring a wooden table surrounded by six white chairs. A cozy carpet covers the floor, and a bookshelf stands nearby, displaying books and potted plants. Greenery can be seen outside through the windows.
Condo in New Paltz
4.75 out of 5 average rating, 60 reviews

Sun-Filled, Spacious 1-Bdrm New Paltz apartment!

The image captures a skyline featuring a mix of modern concrete buildings with varying heights and designs, set against a cloudy sky. A low-rise structure with horizontal lines is visible in the foreground, while vertical towers dominate the background, showcasing urban architecture.
Condo in Albany
4.4 out of 5 average rating, 43 reviews

Empire Plaza View I

A welcoming entryway is highlighted by a wooden staircase leading to an upper level. The open layout reveals a living area with large windows, allowing natural light to brighten the space. A wooden storage bench against the wall offers additional seating.
Condo in Windham
4.75 out of 5 average rating, 4 reviews

airy and lovely space, great views

A modern kitchen area is presented, featuring stainless steel appliances, including a refrigerator and microwave. A bar counter with three dark wooden stools provides seating. Soft lighting is emitted from pendant fixtures above, illuminating the warm wood cabinetry and granite countertops.
Condo in Windham
4.92 out of 5 average rating, 61 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

A light-filled living area features a spacious sectional sofa arranged around a coffee table. The dining area showcases a large wooden table set for six, while a stylish kitchen with a breakfast bar is visible in the background, complemented by modern appliances.
Condo in Hancock

1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub

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Pet-friendly condo rentals

A rustic bedroom features a spacious wooden bed with a patterned blanket, complemented by a decorative bench. Warm wooden paneling adorns the wall, and natural light is let in by a small window, illuminating the inviting space.
Condo in Lanesville
4.89 out of 5 average rating, 28 reviews

Catskills Rustic Chic 4 Bdrm w/ Wood Stove

Guest favorite
A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.
Condo in Litchfield County
4.96 out of 5 average rating, 23 reviews

Meadow View

A cozy living area features a leather sofa with decorative pillows and a round coffee table. Natural light enters through a window covered with sheer curtains. A flat-screen TV is positioned near an electric fireplace, while a dining table with high chairs is set against a tastefully adorned wall.
Condo in Lanesville
4.68 out of 5 average rating, 19 reviews

First-Floor Hunter Condo < 1 Mi to Slopes!

Guest favorite
The living area features a pair of patterned armchairs and a comfortable brown sofa, positioned around a wooden coffee table. A television is mounted on the wall, and a doorway leads to a balcony. Natural light enters through large glass doors.
Condo in Windham
4.91 out of 5 average rating, 11 reviews

Luxury 3-bedroom Condo on Windham mountain

Top guest favorite
The living area features a spacious green sofa facing a wooden coffee table, surrounded by two armchairs. Natural light enters through the windows, illuminating a cozy atmosphere. A dog rests on a warm-toned area rug, while decorative elements include candles and a plant.
Condo in Kerhonkson
5 out of 5 average rating, 33 reviews

Bright & Cozy | Walk to Rail Trail

Top guest favorite
The two-level condo features a combination of wood and stone accents, with a prominent chimney and multiple balconies. Lush greenery surrounds the property, and mountain views are visible in the background under a clear blue sky. A pathway leads to the entrance.
Condo in Hunter
4.95 out of 5 average rating, 65 reviews

Hunter Mountain 2BR Condo - Steps to Mtn /Zip line

A light-filled living area features a tan leather sofa and a glass coffee table, placed atop a patterned rug. A flat-screen television sits on a dark wooden unit. A door leads to additional space, while natural light streams in through a window.
Condo in Windham
4.55 out of 5 average rating, 49 reviews

2. Beautiful, Cozy Condo with view of Windham Mtn

A bright dining area features a large wooden table surrounded by six chairs. Light-colored cabinets and countertops create an inviting kitchen space. Various kitchen appliances and decorative items are displayed on shelves, contributing to the functional and spacious environment.
Condo in Hunter
4.78 out of 5 average rating, 312 reviews

Hiking, fishing,mountain view condo

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Condo rentals with a pool

Guest favorite
A cozy bedroom features rustic wooden walls with decorative hearts. A spacious bed is dressed in light linens, accompanied by a bedside lamp and a small dresser. A guitar leans against the wall, adding a touch of character to the room.
Condo in Hunter
4.88 out of 5 average rating, 92 reviews

Cozy Gem with Mountain Views

Guest favorite
A bright living area is featured, showcasing a cozy arrangement of gray sofas around a circular coffee table. A modern ceiling fan circulates air above while large windows reveal stunning valley views, allowing natural light to fill the room. An electric fireplace adds warmth to the space.
Condo in Windham
5 out of 5 average rating, 24 reviews

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

Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.95 out of 5 average rating, 61 reviews

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

A welcoming living area features large glass doors offering views of the outdoors, with natural light enhancing the space. A comfortable seating arrangement includes a dark blue chair and a sectional sofa, while a stylish large area rug adds warmth. Decorative elements include wall art and a blooming floral arrangement.
Condo in East Jewett
4.94 out of 5 average rating, 31 reviews

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

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.
Condo in Hancock
4.6 out of 5 average rating, 151 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Superhost
A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.
Condo in Lenox
4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

Superhost
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Guest favorite
A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.
Condo in Hancock
4.91 out of 5 average rating, 70 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

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