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

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

An inviting living area features a pool table ready for play and a cozy seating arrangement near a stone fireplace. Light fixtures with a rustic style hang from the ceiling, creating a warm ambiance. A large TV is mounted on the wall, enhancing the entertainment options.
Condo in Hunter

Hunter Condo Practically Ski on Ski Off

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, 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

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

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 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
4.9 out of 5 average rating, 10 reviews

Cozy Luxury Brownstone Stay w/ Yard & Parking

Guest favorite
Condo in Litchfield County
4.96 out of 5 average rating, 26 reviews

Meadow View

Top guest favorite
Condo in Kerhonkson
5 out of 5 average rating, 43 reviews

Explore Minnewaska, rail trail + farm-to-table

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, 3 reviews

Downtown Luxe- Steps to MVP Arena & NYS Capital

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 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
4.56 out of 5 average rating, 52 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
4.77 out of 5 average rating, 315 reviews

Hiking, fishing,mountain view condo

Condo rentals with a pool

Guest favorite
An outdoor swimming pool is surrounded by a chain-link fence, featuring clear blue water and several white lounge chairs positioned beside the pool. Lush green grass and trees frame the area, with a view of a red building in the background.
Condo in Hunter
4.88 out of 5 average rating, 94 reviews

Cozy Gem with Mountain Views

Guest favorite
An outdoor heated pool is surrounded by a spacious patio, with two hot tubs nearby. Lush greenery and vibrant autumn foliage create a scenic backdrop. Multiple lounge chairs are positioned along the poolside, inviting relaxation in a serene setting.
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

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, 32 reviews

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

A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.
Condo in Hancock
4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

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

Guest favorite
A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.
Condo in Hancock
4.88 out of 5 average rating, 32 reviews

Jiminy Peak Apartment

An outdoor heated pool is surrounded by a concrete patio, with lounge chairs positioned nearby. Lush green hills and trees are visible in the background, alongside ski slopes. The pool area is partially shaded by an overhanging roof, allowing for a relaxing atmosphere.
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