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Apartment holiday rentals in Chatham

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Top-rated apartment rentals in Chatham

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Top guest favourite
A panoramic view captures the snowy landscape from the condo, showcasing ski trails on the mountains in the background. The foreground features a plaza with chairs arranged around a fire pit, with skiers and snowboards visible along the paths.
Apartment in Hancock
4.98 out of 5 average rating, 50 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

Top guest favourite
A studio condo features a cozy sleeping area with a patchwork quilt covering a spacious bed. A TV is positioned on a wooden dresser, while a red sectional couch is adorned with various patterned pillows. Ambient light enters through a window, creating a welcoming atmosphere.
Apartment in Hunter
4.95 out of 5 average rating, 536 reviews

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

Top guest favourite
A cozy living room area features a dark leather sofa adorned with decorative pillows. Two lamps light the space, complemented by an ornate side table and a marble coffee table. A large piece of wall art enhances the inviting atmosphere, while a rich area rug covers the wooden floor.
Apartment in Hunter
4.96 out of 5 average rating, 253 reviews

Mint*Cozy*Ski In/Out*Hunter Mt Condo w/Fireplace

Best Ski In/Out Location steps to Ski Lifts & Base Lodge! Immaculate, Spacious with Beautiful Views of Hunter Mnt. All Winter Activities Right there: Skiing, Snowboarding, Snow Tubing. ~Enjoy a Private Deck w/2 Lounge Chairs ~Full Kitchen ~Winter Gear Outdoor Closet ~Front Parking Pass Other Nearby Attractions: Zipline, Skyride, Kaatskill Club, Kaaterskills Falls. Top Safety & Cleanliness: -Self Check-in/out -AirFilter Unit w/UV-C Light & Ionizer -Diffuser w/Essential Oil -Deep Sanitizing

Top guest favourite
Apartment in Windham
4.9 out of 5 average rating, 222 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Superhost
Apartment in Center Square
4.88 out of 5 average rating, 319 reviews

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. Feel free to enjoy a glass of wine in the art gallery.

Superhost
A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.
Apartment in Windham
4.67 out of 5 average rating, 123 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills to enjoy the great outdoors. The complex has a pool, 2 tennis 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. You are in place to enjoy all the skiing, hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

Superhost
A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.
Apartment in Kingston
4.89 out of 5 average rating, 160 reviews

Cozy & walking distance to town *superhost!*

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

Superhost
A winter landscape reveals snow-covered trees and a distant ski mountain, with visible slopes and trails. A nearby house is partially obscured by snow, providing a cozy contrast to the white surroundings. Clouds fill the sky, creating a serene atmosphere.
Apartment in Windham
4.81 out of 5 average rating, 145 reviews

Studio 3 BEDS-SLEEP 4

Light-filled studio in downtown Windham. Beautiful mountain views from your balcony; at night gaze at the moon & stars If you want solitude, this is the place to be! Daytime, take a walk down to the river & enjoy! Walking distance to restaurants & small grocery. Studio is big, with closet, full bathroom, well-stocked coffee area with microwave and refrigerator. Maximum 3 people; 1 double & 2 twins. Check-in: From 4PM off-street parking, Free Wifi /Basic Cable /Linens/Coffee

Guest favourite
A multi-story building features a striking red exterior with a green roof and balconies. Surrounding landscaping includes trees and shrubbery, complementing the natural landscape in the background. The setting is illuminated by soft, natural sunlight under a partly cloudy sky.
Apartment in Hunter
4.89 out of 5 average rating, 100 reviews

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.

Superhost
A spacious living area features a dark sectional sofa and a coffee table, with a mounted flat-screen TV on one wall. The kitchenette, equipped with modern appliances, is visible in the background. A decorative fireplace adds warmth, while a large piece of wall art complements the decor.
Apartment in Lanesville
4.77 out of 5 average rating, 88 reviews

Quiet/cozy, close to slopes apartment

Hop off the powdery slopes and into this cozy 1 bedroom, 1 bath rental! This quiet retreat sits just steps away from the lifts at Hunter Mountain. It offers easy access to local hiking/ski trails (ski in/out), Dolans Lake and local attractions. This rental is the perfect base for all your outdoor adventures no matter the season! Wind down after an adventurous day while enjoying the flatscreen TV with a cup of coffee, tea or hot chocolate.

Guest favourite
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.
Apartment in Hancock
4.91 out of 5 average rating, 74 reviews

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

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

Guest favourite
A spacious living area features large windows offering mountain views. A beige couch with textured cushions sits on a plush carpet. A wooden coffee table is positioned in front of the couch, complemented by a decorative wall hanging. A guitar rests on the floor beside a low bench.
Apartment in East Jewett
4.94 out of 5 average rating, 143 reviews

SereneCatskillsMoutainsGetawayMinutesToSkiResorts

A warm, quiet mountain hideaway where the fireplace glows, 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 couples, 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.

Popular amenities for Chatham apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment 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.
Apartment in Windham
4.33 out of 5 average rating, 3 reviews

2 Bedroom/2Floor Condo Main Street Windham

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.
Apartment in Lanesville
5 out of 5 average rating, 10 reviews

Hunter condo with access to Hunter Mountain

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.
Apartment in Windham
4.75 out of 5 average rating, 4 reviews

airy and lovely space, great views

Private room in Central Avenue
4.73 out of 5 average rating, 11 reviews

The Old Lawmaker's Building.

A cluster of two-story condos is set against a backdrop of lush greenery. The modern structures exhibit a combination of dark and light materials, with large windows that reflect the sunny sky. Neatly trimmed landscaping enhances the welcoming exterior.
Apartment in Hunter

Entire condo in Hunter NY, Gorgeous area- sleeps 6

A spacious sectional couch, upholstered in dark fabric, is arranged around a glass coffee table. The wall is decorated with three art pieces featuring deer antler silhouettes. Light cream curtains frame a window, and a lamp provides additional lighting in the cozy seating area.
Apartment in Windham
4.8 out of 5 average rating, 15 reviews

Ski Windham Mountain ( Catskills, NY)

A well-appointed bedroom features a spacious bed with soft white linens and a wooden headboard. Flanked by matching bedside tables with lamps, the room is complemented by a Jacuzzi tub and a full bathroom visible in the background, creating a relaxing retreat.
Apartment in Lanesville

Hunter Mountain 1BR | Jacuzzi & Fireplace

Apartment in Williamstown

Vacation Village in Berkshires 12/28/25-1/4/26

Pet-friendly apartment rentals

Guest favourite
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.
Apartment in Litchfield County
4.93 out of 5 average rating, 30 reviews

Meadow View

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.
Apartment in Mansion Area
4.7 out of 5 average rating, 27 reviews

Cozy Luxury Brownstone Stay w/ Yard & Parking

Guest favourite
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.
Apartment in Windham
4.92 out of 5 average rating, 12 reviews

Luxury 3-bedroom Condo on Windham mountain

Superhost
A private outdoor hot tub is prominently featured on a spacious deck, overlooking scenic views of the Catskills. Surrounding greenery and gentle hills can be seen in the background, creating a peaceful natural setting.
Apartment in Windham
4.75 out of 5 average rating, 51 reviews

Brand New Outdoor Hot Tub! 1 Bedroom Luxury Suite

Guest favourite
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.
Apartment in Downtown Albany
5 out of 5 average rating, 9 reviews

Downtown Luxe- Steps to MVP Arena & NYS Capital

Superhost
Apartment in Windham
New place to stay

Luxurious spacious 2 BR condo downtown Windham

Top guest favourite
The exterior of the condo is showcased, featuring a two-story structure with a combination of red siding and stone accents. Balconies with wooden railings extend from the upper levels, and a prominent stone chimney rises against a cloudy sky.
Apartment in Hunter
4.96 out of 5 average rating, 70 reviews

Hunter Mountain 2BR Condo - Steps to Ski Slopes!

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.
Apartment in Hunter
4.77 out of 5 average rating, 318 reviews

Snowboarding skiing Mountain View condo

Apartment rentals with a pool

Top guest favourite
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.
Apartment in Hunter
4.89 out of 5 average rating, 99 reviews

Cozy Gem with Mountain Views

Guest favourite
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.
Apartment in Windham
5 out of 5 average rating, 29 reviews

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

Top guest favourite
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.
Apartment in Hancock
4.95 out of 5 average rating, 63 reviews

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

Guest favourite
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.
Apartment in Hancock
4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

Guest favourite
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.
Apartment in Windham
5 out of 5 average rating, 7 reviews

Luxury Ski in Ski out Condo + Amenities

Guest favourite
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.
Apartment in Windham
5 out of 5 average rating, 5 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

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.
Apartment in Hancock
4.61 out of 5 average rating, 157 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Ski Jiminy Peak - 1BD

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