Become a host

Condo vacation rentals in Chatham

Find and book unique condos on Airbnb

0 of 0 items showing
1 of 3 pages

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Guest favorite
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

A historic three-story building is positioned along a main street. The façade features large windows and a decorative roofline. A grey vehicle is parked in front, and nearby structures can be seen, illustrating the vibrant atmosphere of the area.
Condo in Windham

2 Bedroom/2Floor Condo Main Street Windham

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 cluster of brown wooden condos is set against a backdrop of autumn foliage on a hillside. The buildings feature multiple balconies and large windows. Surrounding greenery includes well-maintained shrubs and trees, complementing the scenic landscape.
Condo in Hunter
4.48 out of 5 average rating, 42 reviews

Spacious 3 BR Condo Steps Away From Slopes!

A spacious living room features a large green sectional sofa, complemented by a stylish arc floor lamp. A coffee table is positioned in the center, and a television is mounted on a white entertainment unit. Natural light filters through sheer curtains, creating a bright atmosphere.
Condo in Hunter
4.74 out of 5 average rating, 19 reviews

Lavish Skiing Condo With Fireplace Steps To Slopes

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 Center Square
4.4 out of 5 average rating, 45 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

Pet-friendly condo rentals

Superhost
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 Mansion Area
4.79 out of 5 average rating, 14 reviews

Cozy Luxury Brownstone Stay w/ Yard & Parking

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
4.93 out of 5 average rating, 28 reviews

Meadow View

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
4.92 out of 5 average rating, 12 reviews

Luxury 3-bedroom Condo on Windham mountain

Top guest favorite
Condo in Kerhonkson
5 out of 5 average rating, 45 reviews

Explore Minnewaska, rail trail + farm-to-table

Guest favorite
A modern living area features a comfortable leather sofa with decorative pillows, accompanied by a rustic coffee table. A large television is positioned on a sleek stand. The kitchen is visible, showcasing dark cabinetry, stainless steel appliances, and natural light flowing through a window.
Condo in Downtown Albany
5 out of 5 average rating, 5 reviews

Downtown Luxe- Steps to MVP Arena & NYS Capital

Guest favorite
An open living space features vaulted ceilings supported by exposed wooden beams. A comfortable sofa with colorful cushions is positioned beside a coffee table, while a dining table with chairs occupies the other side. Natural light floods in through large windows, creating a bright and inviting environment.
Condo in North Adams
4.96 out of 5 average rating, 89 reviews

Newly renovated 2BR on historic Eagle Street.

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
4.96 out of 5 average rating, 67 reviews

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

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
4.77 out of 5 average rating, 315 reviews

Hiking, fishing,mountain view condo

Condo rentals with a pool

Top 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
4.89 out of 5 average rating, 96 reviews

Cozy Gem with Mountain Views

Top 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, 25 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

Guest favorite
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 spacious living area is highlighted by large windows that provide views of the surrounding landscape. A modern fireplace is set against a stone feature wall, while comfortable seating options include a sectional sofa and accent chairs. A flat-screen TV is mounted above a stylish entertainment unit.
Condo in Windham
5 out of 5 average rating, 4 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

Guest favorite
An aerial view captures the Whisper Creek condo set against a snowy mountain backdrop, with ski slopes winding down the hillside. The landscape features a mix of pine trees and winter terrain, while the luxury building connects to the scenic outdoors.
Condo in Windham
5 out of 5 average rating, 6 reviews

Luxury Ski in Ski out Condo + Amenities

Superhost
A winding gravel path meanders through a landscape filled with autumn foliage. Tall trees display vibrant orange and yellow leaves, while golden grasses border the trail, creating a serene natural setting. The scene suggests a peaceful retreat into nature.
Condo in Windham
4.72 out of 5 average rating, 289 reviews

Autumn Retreat w/wood burning fireplace

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, 154 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Columbia County
  5. Chatham
  6. Condo rentals