
Apartment vacation rentals in Chatham
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Top-rated apartment rentals in Chatham
Guests agree: these apartments are highly rated for location, cleanliness, and more.

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!

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!

King Bed, Wi-Fi, 2m Ski Resort
Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Youtube TV with NFL Pack

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.

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.

Cosy Catskill Casita in the Middle of Village
The Casita is a studio apartment comfortable for solo travellers, couples or just two folks who don't mind sharing a bed! We’ve endeavored to make it a comfortable stay for a weekend or even longer, with all basic amenities, a queen size bed, standing shower bathroom, and kitchenette. Although it is an apartment on the ground floor of my house, you will have your privacy with a separate entrance off of the driveway which is for guest use during the stay.

Catskill Village House - Mountain View Studio
Our largest option, the Mountain View Suite incorporates high ceilings, and mountaintop views from a raised dining area to provide a large and light oasis. Located on the second floor, the suite features custom antique accents and original artwork that evoke a sense of adventure. The room includes a large bath with clawfoot tub and shower, kitchenette, and sleeper sofa. Custom queen mattress (featured at the Four Seasons NYC), organic cotton sheets.

Gorgeous Getaway, close to everything!
The apartment is spacious, bright, peaceful and very private. There is a coded lock, and your own front entry and spacious front porch. Located on a quiet street, just slightly off the beaten path yet within a short walk to all of the best restaurants and shopping Hudson has to offer. A full kitchen will also allow for some chill out time or a family meal if that is more your speed. A beautiful and convenient refuge.

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.

Serving Sexy Historic Hudson Realness Steps from Warren St
Feast your eyes on the drop-dead gorgeous dining room and then get ready to have a feast because the kitchen is fully equipped for everything from cocktails to the main course. Or simply take in the dramatic pops of color and sexy decor sprinkled throughout the space. Unwind after a long day of antiquing or exploring on a cozy outdoor sectional in the backyard garden.

A Lovely Historic Apartment
A historic, Italianate Victorian located on a quiet street in downtown Hudson, two blocks away from charming Warren Street. Our property has a fenced-in backyard filled with lovely greenery, lush gardens, and meditative places to lounge. Designed with comfort and beauty in mind, our chic, peaceful nest is the perfect place to land in Hudson.

Cemetery Schoolhouse 2
A nice place to hide out for the winter and across the street from UMH. We are a 7 min stroll to the top of Warren, This is a park setting, totally removed from any living soul with acres to stroll and explore!! I'm so sorry we have been regulated to only accepting a minimum of 30 nights
Popular amenities for Chatham apartment rentals
Weekly apartment rentals

Station House 1E Private Room & Bath

Light Filled 2+BR in the Heart of Hudson

Hip Warren Street Apartment

Historical Downtown 1 Bedroom Apartment

Modern Luxury & Victorian Charm: The Bird in Hand

Steps to MoCA Near SKI: 2bd + SAUNA!

Hist. Troy River acc. Modern Apt

Warren St. Ensuites - Pets allowed
Private apartment rentals

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Serene Suite near Skiing, Walk to Restaurants

Chic Hudson Apartment - In the heart of Hudson, NY

Cozy private apartment in Rhinebeck Village

Kinderhaus Loft in Chatham, New York

Spacious, Bright & Airy! Tangerine Dream Suite

Townhouse apt+cntrl+prking+yrd

Woodland Neighborhood Retreat
Apartment rentals with a hot tub

Berkshire Mountain Top Chalet

Ski-In Ski-Out Loft Lift & MT. Views

Relaxing Spa Retreat~Gorgeous View~Walk to Village

Cozy Ski Retreat

Luxe Ski Getaway Base of Jiminy

Burnt Knob Mountain Escape

Mountain Top Hot Tub Suite Hiking & Falls 5 min

Dog Friendly Hudson Valley Escape with Hot Tub
Quick stats about apartment rentals in Chatham

Nightly prices starting at
Chatham vacation rentals start at G$6,272 GYD per night before taxes and fees

Verified guest reviews
Over 50 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chatham rentals

4.9 Average rating
Chatham stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Howe Caverns
- Windham Mountain
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Saratoga Spa State Park
- Taconic State Park
- Norman Rockwell Museum
- Ski Sundown
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village




