Apartment holiday rentals in Chatham

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Top-rated apartment rentals in Chatham

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Guest favourite

A clear swimming pool is enclosed by a fence, featuring a ladder for easy access. Lush greenery and the mountains are visible in the background, with lounge chairs positioned nearby. The scene is set under a bright blue sky with wispy clouds.

Apartment in East Jewett

4.94 out of 5 average rating, 156 reviews

Stunning Views • Bright 2-BR • Pool • Near Farm • Lakes • Farm

A quiet mountain hideaway where 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 families, 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. Easy drive to charming little towns - Windham, Hunter , Tannersville . Swimming pool on premises , CD Lane Lake with beach and free boat

Guest favourite

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 Albany

4.78 out of 5 average rating, 60 reviews

2BR w/ Parking + deck - Near Downtown & MVP Arena

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.

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

4.94 out of 5 average rating, 562 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

Superhost

Apartment in Albany

4.86 out of 5 average rating, 29 reviews

The Dove: A Peaceful Large Studio Private Bathroom

Welcome to The Dove’s Nest, a cozy and quiet space perfect for solo travelers or couples. Located in a peaceful neighborhood in Albany, it's a great place to relax or get some work done. What you’ll get: - Bedroom, Livingroom, and bathroom, - Comfortable bed and linens - Small sitting area - Washer and Dryer - Smart - TV - Wi-Fi - Mini fridge, microwave, and coffee/tea setup - Full Private bathroom - Shared entrance and available parking Come enjoy a simple, calm stay at The Dove’s Nest.

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

4.86 out of 5 average rating, 118 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 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

4.69 out of 5 average rating, 127 reviews

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills. The complex has a pool, tennis, pickleball & basketball 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. Your place to enjoy all the hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

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, 116 reviews

Cozy Gem with Mountain Views

A cozy apartment located less than a mile away from premier skiing and snowboarding at Hunter Mountain. Our place is located in a lovely community that has plenty of space to enjoy some quality time with family and friends. This is our home away from home and you can experience lot of personal touches throughout the apartment such as custom wood work, family photos and seasonal decoration. We can not wait for you to enjoy the beauty of Catskill mountains.

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

4.88 out of 5 average rating, 178 reviews

Historic Rondout Home | Walk to Waterfront

Welcome to our comfortable two-bedroom home in Kingston’s historic Rondout neighborhood. It’s an easy home base for couples, friends, families, and solo travelers—just a short walk from the waterfront and some of Kingston’s best restaurants and shops. *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

Guest favourite

Apartment in Albany

4.89 out of 5 average rating, 359 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.

Guest favourite

A modern kitchen is visible, featuring stainless steel appliances and ample storage cabinets. A dining table set for four is in the foreground, complete with glassware and decorative green accents. Natural light fills the space, highlighting the open floor plan that leads into the living area.

Apartment in Lenox

4.89 out of 5 average rating, 91 reviews

Heart of Lenox!! - Renovated downtown apartment

Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road you will find the historic Red lion Inn in Stockbridge or Norman Rockwell Museum.

Superhost

Apartment in Lanesville

4.89 out of 5 average rating, 158 reviews

Cozy Downtown Hunter Mountain Getaway

Keep it simple at my peaceful and centrally-located loft. You are at the footsteps of Hunter Mountain, right beside Dolan's Lake and a very short drive to all of Village of Hunter restaurants, bars, cafes, hikes and conveniences. You can easily walk to Hunter Mountain and the Trailways Bus line. The condo has its own wifi and 2 roku TV’s.

Guest favourite

A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.

Apartment in Adams

4.74 out of 5 average rating, 68 reviews

Downtown Adams Vintage Getaway

Your family will be close to everything when you stay at this centrally-located place. Walk to the Adams Theater, rail trail, grocery store, restaurants, shops, or take a quick drive to MassMoCA, Jiminy Peak, or Greylock Glen. This is the perfect location for all north county has to offer. One free parking spot in back of building.