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Apartment vacation rentals in Chatham

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Top-rated apartment rentals in Chatham

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An airy interior showcases exposed wooden beams and a blend of modern and rustic decor. A kitchen counter with stools is positioned towards the left, complemented by a dining table with chairs in the center. A cozy bedroom is visible through the doorway on the right.

Apartment in Philmont

4.89 out of 5 average rating, 123 reviews

Beautiful space in the heart of Philmont

Enjoy the elegant ambience of this airy and bespoke space, just two doors up from the excellent restaurant Local 111, as well as the Co-op, where you can pick up delicious local produce, meats, and baked goods. A couple blocks from the Philmont Pub, another fantastic place to eat and enjoy the evenings. Minutes from Hudson, this town is literally in the center of Columbia County. A short drive to Catamount, Bash Bish, the Hudson River, the Catskills, the Berkshires, no end of places to explore!

A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.

Apartment in Copake Falls

4.91 out of 5 average rating, 346 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Two turquoise Adirondack chairs are positioned on a grassy area, facing the entrance of a light blue house. Lush foliage surrounds the space, with trees and colorful shrubs enhancing the natural setting. A private porch features white railings, adding architectural interest.

Apartment in Hudson

4.96 out of 5 average rating, 193 reviews

Studio Oasis nr Warren St w porch & yard

Oasis in midst of downtown Hudson, 2 blocks fr Warren St, short walk fr Amtrak, 1/2 block fr Empire State Trail. Spacious, sunny studio apartment w fenced in yard, park-like setting & private porch to relax, have a meal or watch the world go by. Inside this elegant 1850 home, you’ll find bedroom, living room and work areas, full kitchen w dining table, and a large bathroom w clawfoot tub and a walk in shower. Original architectural details have also been preserved with care. Come, and enjoy!

A bright living area features a comfortable sofa adorned with decorative pillows in relaxing tones. A vibrant yellow armchair adds a pop of color, while natural light fills the space through large windows with soft curtains. A round coffee table sits at the center, accompanied by a sleek TV stand.

Apartment in Hudson

4.97 out of 5 average rating, 311 reviews

Stylish Hudson Getaway

Enjoy our one bedroom home in the heart of beautiful Hudson, New York. Steps away from the best shops and restaurants Warren Street has to offer, our apartment is on a beautiful residential street with historic views. Introduce yourself to our town with the peace of mind that when you return to this Airbnb, you can relish in the delight of organic cotton sheets, lush robes and slippers, an assortment of organic teas and coffee, and some of the best products from our sweet little city.

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 127 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Top guest favorite

A cozy seating area features a large, woven hanging chair with a white cushion and a bright green accent pillow. A textured pouf and a small side table complement the space, which is surrounded by large windows offering views of the mountains and natural light.

Apartment in Freehold

5 out of 5 average rating, 316 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

Top guest favorite

A spacious bedroom features a wooden four-poster bed adorned with green and white pillows. A dining table with two chairs sits in one corner. Soft lighting is provided by a lamp and two hanging chandeliers, creating a calm ambiance.

Apartment in Hillsdale

4.99 out of 5 average rating, 219 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

Top guest favorite

A spacious bedroom is showcased with a wooden bed frame and comfortable linens, complemented by two bedside lamps. Natural light floods the space through windows adorned with simple treatments, and a cozy rug lies beneath. A small table and a decorative plant add warmth to the inviting atmosphere.

Apartment in Valatie

4.95 out of 5 average rating, 200 reviews

Holland House: Modern Rustic Guest Apartment

Thoughtfully designed two-bedroom apartment located above a former millinery shop built in 1880. Beautiful natural light. Mix of vintage and modern amenities, including two guest bedrooms, full kitchen and bath, high speed wifi, in-unit laundry and work desks. Private tree-shaded back porch overlooking Kinderhook Creek and Pachaquack Preserve. 20 minutes to Hudson. 30 minutes to Albany, the Berkshires and the Catskills.

A spacious front porch is framed by white columns and features two seating areas. Lush greenery encompasses the porch, with a flowering rhododendron bush in the foreground. The blue sky is dotted with clouds, enhancing the inviting atmosphere of the outdoor space.

Apartment in New Lebanon

4.96 out of 5 average rating, 108 reviews

Airy apartment at the old boarding house

Distinctive 2-bedroom with lots of windows and light and a kind of shabby elegance. It's half of a Greek Revival house from 1900 on a country lane at the foot of the Berkshires. Enormous master bedroom with dressing room, 2nd bedroom with twin beds, lovely living room, separate dining room, full kitchen. Big covered front porch for eating outside, with grill, table and an acre of orchard outside too.

A historic Greek Revival house is seen from the front yard, featuring a white facade complemented by green trees. A red door serves as a focal point, with several windows allowing natural light. The yard is bordered by a wooden fence and includes well-maintained grass.

Apartment in Coxsackie

4.93 out of 5 average rating, 145 reviews

Lovely 1 bedroom suite in historical house

Located just outside historic downtown Coxsackie, this newly renovated suite in a 220 year old Greek Revival house is within easy walking distance to tiny downtown Coxsackie and its restaurants and shops. 25 minutes to Hudson, 45 min-1 hour to the Catskill Mountains. I live above and next door with my dog George. It’s an old house, with all attendant creaks and charms.

A bright dining area features a wooden table centered under a woven pendant light, surrounded by white chairs. A fresh floral centerpiece accompanies a bowl of fruit. Doorways to adjacent rooms are visible, enhancing the open layout and inviting atmosphere.

Apartment in Hudson

4.94 out of 5 average rating, 392 reviews

Light Filled 2+BR in the Heart of Hudson

This big, bright and beautiful historic home is located on a quiet street, two blocks away from the Main Street in Hudson. Within a few minutes walk you will be surrounded by all the antique shops, cafés, restaurants, and the farmers market. Yet, if you are looking for a quiet sanctuary, with tranquil lake walks just one block away, this is a place for you.

Top guest favorite

The exterior view of a spacious two-story home is presented, featuring a wraparound porch supported by white columns. Large windows illuminate the façade, while vibrant greenery from surrounding trees and gardens enhances the tranquil atmosphere.

Apartment in Great Barrington

4.96 out of 5 average rating, 386 reviews

Private En Suite in Beautiful Victorian

The room is light and airy with morning sun and the shade of the large front porch in the afternoon. This is a place to enjoy a meal or just lounge and relax with a view of the gardens and surrounding woods. This space features a private entrance, a kitchenette and full bathroom and very comfortable queen bed. In mid July 2024 we added air conditioning.

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Popular amenities for Chatham apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Top guest favorite

A cozy bedroom is framed by an open doorway, featuring a wooden accent wall and a decorative headboard. A light fixture hangs above, and a bright pink pillow adds a splash of color to the white bedding, complemented by a mustard-colored throw blanket at the foot of the bed.

Apartment in Hudson

4.98 out of 5 average rating, 185 reviews

Lower Warren Street Picture-Perfect 2-Bedroom Apt

An inviting entrance area showcases a vintage Coca-Cola vending machine. A wooden door leads into a room with a detailed patterned wallpaper. A decorative stove stands prominently, complementing the warm aesthetic of the space.

Apartment in Lenox

4.88 out of 5 average rating, 196 reviews

Station House 1E Private Room & Bath

Top guest favorite

A spacious living area features large windows with natural light, framed by elegant drapes. A dark leather couch is positioned near a decorative area rug. A wooden dining table for two and a green accent chair complement the space, while a cozy fireplace adds charm.

Apartment in Washington Park

4.97 out of 5 average rating, 228 reviews

Washington Parkside 1 Bedroom In 1800s Brownstone!

A cozy sitting area features a plush armchair and a wicker chair, both positioned near a coffee table. Natural light enters through two large windows, illuminating the patterned wallpaper. A green indoor plant adds a touch of nature, and a media unit displays a TV and various books.

Apartment in Athens

4.93 out of 5 average rating, 217 reviews

1 bdrm apt in Athens on the Hudson

A cozy living space features vintage art deco posters mounted on the walls. Sunlight filters through the window, illuminating a cushioned sofa and a wooden bar area. Light-colored walls and detailed wallpaper add visual interest, enhancing the room's eclectic style.

Apartment in Coxsackie

4.92 out of 5 average rating, 171 reviews

Art Deco cocktail lounge themed 1BR- Nightcap245

Top guest favorite

A cozy sleeping area features a spacious bed with white bedding and a decorative pillow. A low table with a bedside lamp stands beside the bed, and a small seating area with a blue and white striped chair is visible. A patterned area rug adds warmth to the floor.

Apartment in Hudson

4.98 out of 5 average rating, 112 reviews

Private Hudson pied-à-terre; blocks from Amtrak

A spacious living area features a comfortable grey sofa and a marble-topped dining table with two chairs. A smart TV sits on a wooden stand against a light wall. Sunlight filters through sheer curtains, illuminating the room. A bedroom is visible in the background.

Apartment in Hudson

4.92 out of 5 average rating, 230 reviews

Studio/Guest Suite Minutes from Warren St.

Two pinball machines are positioned against a dark blue wall, featuring vibrant art and illuminated playfields. The machines offer a mix of classic and modern designs. A person stands nearby, engaging with the machines, while additional board games are visible on shelves in the background.

Apartment in Troy

4.96 out of 5 average rating, 131 reviews

Retro Pinball Arcade/Board Game AirBnB

Private apartment rentals

A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.

Apartment in Amenia

4.93 out of 5 average rating, 115 reviews

Amenia Main St Cozy Studio

A spacious living area displays a mix of seating options, including a blue couch and two accent chairs. Natural light filters through large windows, highlighting the wooden beams above. A wooden table sits in the foreground, with a ladder leading to the loft visible in the background.

Apartment in Earlton

4.94 out of 5 average rating, 302 reviews

Sweet Farm Stay

The kitchen features modern appliances, including a black refrigerator and stainless-steel oven. A wooden dining table sits in the center, adorned with a bowl of fresh fruit. Shelves above display plants and kitchenware, while natural light filters through the windows, creating an inviting ambiance.

Apartment in Kingston

4.97 out of 5 average rating, 215 reviews

Renovated apartment in midtown Kingston

Top guest favorite

The kitchen area features dark cherry wood cabinets and a black granite countertop, with a modern sink and decorative bowl. An arched pass-through opens to the living space, which includes a beige sofa and a wall-mounted TV. Natural light enters from the adjacent room.

Apartment in Troy

4.95 out of 5 average rating, 159 reviews

Beautiful modern unit, feels like home!

A cozy living space is illuminated by a warm table lamp on a simple wooden table, complemented by a small speaker. Natural light filters through two large windows dressed with airy curtains. A piece of art decorates the wall, adding character to the room.

Apartment in Stone Ridge

4.89 out of 5 average rating, 594 reviews

Cozy Apartment with Sauna in Historic Stone Ridge

A bright and inviting living room features a floral-patterned couch and large windows adorned with green curtains. Decorative plant stands filled with various plants enhance the space, while a stained glass light fixture casts a warm glow over the area. A cozy atmosphere is created with soft lighting.

Apartment in Winsted

4.91 out of 5 average rating, 395 reviews

Gateway to the Berkshires

The open living area features large windows allowing natural light to fill the space. A sleek black couch and a leather armchair complement a dining table with wooden chairs. A flat-screen television is mounted on the wall, enhancing the room's modern feel.

Apartment in Hudson

4.97 out of 5 average rating, 284 reviews

Thomas Jenkins Guesthouse hudson

The exterior of the Historic Hillsdale House is shown, featuring a two-story wooden structure with a sloped roof. A covered porch with seating is visible, illuminated by soft lighting. Several windows are adorned with shutters, and the inviting entryways lead into the building.

Apartment in Hillsdale

4.89 out of 5 average rating, 108 reviews

The Studio at the Historic Hillsdale House

Apartment rentals with a hot tub

Top guest favorite

An open-concept living space features a modern kitchen with wood cabinetry and granite countertops. A cozy seating area includes a large smart TV. The scene transitions to a scenic view of a calm body of water surrounded by lush greenery and distant hills, reflecting the serene landscape.

Apartment in Saugerties

5 out of 5 average rating, 6 reviews

Esopus Creekfront Getaway | Sauna & Kayak I HotTub

A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.

Apartment in Hancock

4.95 out of 5 average rating, 44 reviews

Ski-InSki-Out Loft Lift&MT.Views

A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.

Apartment in Hancock

4.76 out of 5 average rating, 17 reviews

Artsy loft surrounded by fall foliage with hot tub

Top guest favorite

A vibrant sunrise casts shades of orange and yellow across the sky, illuminating the lush green landscape below. A serene pond is nestled within the meadow, surrounded by trees that display autumn colors, providing a tranquil setting for outdoor relaxation.

Apartment in Acra

4.99 out of 5 average rating, 162 reviews

Burnt Knob Mountain Escape

An outdoor space features a hot tub surrounded by a gravel area. Two lounge chairs and a glass table are placed near a striped rug. Potted plants are hung along the wooden fence, enhancing the cozy atmosphere.

Apartment in Kingston

4.9 out of 5 average rating, 200 reviews

Charming Pet Friendly Getaway w Hot Tub & Fire Pit

An outdoor recreational area is illuminated at night, featuring a billiard table under a gazebo. Guests are seated around picnic tables, enjoying their time. Soft lighting enhances the ambiance, while the yard displays green grass and surrounding structures.

Apartment in Watervliet

4.95 out of 5 average rating, 81 reviews

Uptown Watervliet

A private hot tub sits on a wooden deck surrounded by snow-covered trees. The tub is partially covered, emphasizing tranquility amid a winter landscape, while a wooden fence encloses the area, offering privacy.

Apartment in Tannersville

4.88 out of 5 average rating, 331 reviews

Mountain Top Hot Tub Suite Hiking & Falls 5 min

A refreshing in-ground pool is surrounded by a patio area, featuring colorful lounge chairs and vibrant flower pots on either side. The pool area is enclosed by a fence, with a shaded seating area visible in the background, enhancing the tranquil outdoor setting.

Apartment in Pittsfield

4.93 out of 5 average rating, 81 reviews

Berkshire’s Sweet Spot-Spa/Pool/Fall Foliage

Destinations to explore