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Apartment holiday rentals in Chatham

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Top-rated apartment rentals in Chatham

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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, 23 reviews

Cozy Luxury Brownstone Stay w/ Yard & Parking

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.

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.

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, 523 reviews

Hunter Mtn. Close Clean Cozy 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, 220 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.

Guest favourite
Apartment in Center Square
4.9 out of 5 average rating, 304 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, 122 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
4.91 out of 5 average rating, 159 reviews

Cozy & walking distance to town *fall dates!*

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
An inviting outdoor hot tub is positioned on a wooden deck, overlooking expansive views of the lush Catskills. The serene water bubbles gently, with the surrounding trees and distant mountains creating a tranquil backdrop.
Apartment in Windham
4.94 out of 5 average rating, 18 reviews

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite

➤ Nature Immersive Retreat in the Catskills, with Haus Windham Luxury Vacation Rentals! • Serene Getaway near Windham Mountain & Panoramic Views. • 2-3 minute drive to the Ski Lifts! • PRIVATE BRAND NEW OUTDOOR HOT TUB! • Parachute Brand bedding & linens • Wood Fireplace, BBQ • Huge Outdoor Balcony ★ Daily Housekeeping Included During Stay ➤ 2 BD Suite (1 King/2 queen) - Full Kitchen, Living area, Outdoor Hot tub, BBQ, & Fireplace Luxurious 5-Star Suites, in the heart of Windham

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, 139 reviews

MountainViews2BR/15MinToSkiResorts/Windham/Hunter

Spacious two-bedroom with stunning mountain views! Bright sunny open space layout and a modern, comfortable design perfect for relaxing or working remotely. Wake up to natural light, unwind in style, and experience the peace of mountain living with all the comforts of home. Cozy up by the fireplace after a day of skiing or exploring and savor the calm atmosphere, and let the serene surroundings recharge you. Ideal for couples, friends, or families seeking a cozy yet elegant getaway.

Guest favourite
The living area features a pull-out sofa, a woven storage ottoman, and a coffee table on a patterned rug. A kitchen island with seating is visible, alongside a black refrigerator and a wood-burning fireplace. Soft lighting creates a comfortable ambiance.
Apartment in Hunter
4.93 out of 5 average rating, 54 reviews

Cozy Slopeside Condo @ Hunter Mountain

Contemporary condo steps away from the slopes at Hunter Mountain! Avoid busy resort parking by staying right on the mountain. Simply walk 350 steps to the end of the road and you will be on Hunter’s Briar Patch trail (rated green for beginners). From there, you can jump on your skis and head down the mountain to access the base lodge, lifts, and everything the resort has to offer. You can even ski back to the condo for mid-day breaks and lunch!

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
4.9 out of 5 average rating, 73 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.

Popular amenities for Chatham apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favourite
A inviting living area showcases a stone fireplace and wooden furniture. A rectangular dining table with chairs occupies the space, complemented by a comfortable seating arrangement. Natural light filters through large windows, highlighting a patterned area rug that adds warmth to the room.
Apartment in Hunter
4.81 out of 5 average rating, 26 reviews

Condo on Hunter Mt.

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.
Apartment in Hunter
4.48 out of 5 average rating, 42 reviews

Hunter Mountain Condo | Walk to Lifts & Town

Superhost
An open living space is shown featuring a modern dining table surrounded by four chairs. Natural light enters through skylights, illuminating the area. A wooden staircase leads to a loft, while a kitchenette is visible in the background, enhancing the inviting atmosphere.
Apartment in Windham
4.25 out of 5 average rating, 8 reviews

Outdoor HotTub/Deck, Views! Luxury 2BR Suite, Loft

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

The Old Lawmaker's Building.

Superhost
An aerial view showcases the expansive 22-acre estate nestled in the Catskills, surrounded by lush green trees. The property features a spacious lawn and access to hiking trails, with the scenic mountains serving as a backdrop, inviting guests to relax in nature.
Apartment in Windham
4.75 out of 5 average rating, 4 reviews

New Outdoor Hot Tub & Deck! 1 Bedroom Luxury Suite

Superhost
A spacious living room is highlighted by two comfortable sofas and a lounge chair, arranged around a coffee table. A dining table for four is positioned near large windows, allowing natural light to fill the area. A flat-screen TV is mounted on the wall.
Apartment in Windham
4.74 out of 5 average rating, 73 reviews

4.Special long term prices - escape the City!

A spacious living area features large windows allowing natural light to flood the room. A contemporary sofa, accent chairs, and a decorative coffee table are arranged around an electric fireplace, while a mounted Smart TV adds convenience.
Apartment in Washington Park

Albany Vacation Rental w/ State Capitol Views!

Apartment in Melrose
4.75 out of 5 average rating, 12 reviews

The Dove's Nest of Albany

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 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
4.79 out of 5 average rating, 48 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, 6 reviews

Downtown Luxe- Steps to MVP Arena & NYS Capital

Guest favourite
A spacious living area is highlighted by a comfortable sofa adorned with various cushions. A television is mounted on an accent wall, while light wood furnishings add warmth. A loft with a ladder can be seen in the background, enhancing the room's vertical space.
Apartment in Windham
4.85 out of 5 average rating, 92 reviews

3.Special long term prices - escape the CITY

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)

Top guest favourite
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.
Apartment in Hunter
4.96 out of 5 average rating, 69 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.
Apartment in Hunter
4.77 out of 5 average rating, 317 reviews

Hiking, fishing,mountain view condo

Superhost
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.
Apartment in Windham
4.58 out of 5 average rating, 55 reviews

2. Beautiful, Cozy Condo with view of Windham Mtn

Apartment rentals with a pool

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, 98 reviews

Cozy Gem with Mountain Views

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.
Apartment in Hancock
4.89 out of 5 average rating, 9 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

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, 62 reviews

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

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

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.
Apartment in Windham
4.73 out of 5 average rating, 291 reviews

Autumn Retreat w/wood burning fireplace

Guest favourite
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.
Apartment in Hancock
4.85 out of 5 average rating, 34 reviews

Jiminy Peak Apartment

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, 156 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

A cozy bedroom is highlighted by a plaid bedspread draped over a spacious bed. A wooden nightstand with a lamp stands beside the bed, while large windows allow natural light to fill the room, offering views of the surrounding mountains.
Apartment in Lanesville

Hunter Mtn 3BR Condo | Ski-In/Ski-Out & Spacious

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