
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.

Historic,Famous,Iconic, Unforgettable Berks Escape
PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

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.

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" Smart TV

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!

Serene Suite: Hudson & Berkshires, Walk to Brewery
A peaceful, highly rated private suite in the heart of historic Hillsdale, where the Hudson Valley meets the Berkshires. Walk to shops, restaurants, a brewery, cooking school, grocery, wine and liquor store. Minutes to Hilltown, the Harlem Valley Rail Trail, scenic hikes, and beautiful drives, with galleries, antiques, live music, and cultural gems nearby. A serene, perfectly located home base for spring dining, exploring, and unwinding.

Catskill Village House - Garden Studio
A serene space inspired by the contemplative calm of the open water, our Garden Suite features a large living room, outdoor deck and shared garden, private bathroom with claw foot tub and shower, and sleeper sofa. Original artwork, a custom made kitchenette, and dining area add to this beautiful and generous space. Custom Queen Size Mattress (featured at the Four Seasons NYC), organic cotton sheets. Free WIFI (150mb/12mb) and AC.

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.

Marie's Place
This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters. Ac units are installed from June through September.

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.

Colonel Hasbrouck’s 1735 Stone House, Garden Level
Right in Kingston's historical Stockade District, this garden-level apartment blends original 18th-century decorative features like dutch doors and a large stone hearth with modern amenities like a washer/dryer and easy keyless entry. It's part of the Colonel Abraham Hasbrouck House, a registered historical landmark built in 1735.

Above SpringRise
Newly renovated, top floor apartment on Main Street in the historic district of Catskill. Overlooking both the Catskill Creek and the Catskill Mountains, this floor-through apartment is just 10 minutes to Hudson, 5 minutes to three Nature preserves and 15 minutes to Kaaterskill Falls.
Popular amenities for Chatham apartment rentals
Weekly apartment rentals

1 bdrm apt in Athens on the Hudson

Studio/Guest Suite Minutes from Warren St.

Tangerine Dream~king suite/ perfect for two

Bright, Charming 3-BR with Garden in Heart of Town

Thomas Jenkins Guesthouse hudson

Vibrant Lower Warren Street Writing Retreat

Escape to a Sleek, Serene Studio on the Riverbank

Sunny, Spacious & Central: Bowler
Private apartment rentals

Ground Floor Apartment on Hudson River

Light Filled 2+BR in the Heart of Hudson

Spacious Historic 3BR/1.5BA Troy Washington Park

Jewel above the Pub with a view. Walk everywhere!

Private Hudson pied-à-terre; blocks from Amtrak

COLD SPRING

Whiteley Hideaway- walk to Mass MoCA and Downtown

Secluded but not isolated Berkshire Retreat
Apartment rentals with a hot tub

Mountainside Condo Ski on/off

Berkshire Mountain Top Chalet

1st FL Mtn View Woodland Suite Jiminy Peak Sleeps4

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

Mountain view apartment, 5mins to Ski Area!

Burnt Knob Mountain Escape

Charming Pet Friendly Getaway w Hot Tub & Fire Pit

Mountain Top Hot Tub Suite Hiking & Falls 5 min
Quick stats about apartment rentals in Chatham

Nightly prices starting at
Chatham vacation rentals start at G$6,275 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

5 Average rating
Chatham stays are highly rated by guests—averaging 5 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Saratoga Race Course
- Berkshire East Mountain Resort
- Howe Caverns
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Taconic State Park
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Bousquet Mountain Ski Area
- June Farms
- Walkway Over the Hudson State Historic Park
- Ski Sundown
- Saratoga Spa State Park
- Millbrook Vineyards & Winery
- Naumkeag
- Poets' Walk Park





