Town of Chatham, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Chatham, New York on RentalSaver.com!

Town of Chatham Rentals

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VRBO
Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Large dining room, spacious kitchen with cozy sofa and chairs in from of wood burning stove, 2 bedroom, library/ yoga / ...
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VRBO
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VRBO
9 acres of elegant gardens, rolling lawns, wooded paths and a private pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Explore 9 private acres of elegant gardens, rolling lawns, meadows, and wooded paths, complete with an (unheated) privat ...
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VRBO
From $702 per night (USD)
VRBO
A charming private 3-bedroom country house with scenic views and sprawling lawn
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience Old Chatham like a local in this 3-bedroom country house/chateau. This stunning property features 3 bedrooms ...
From $702 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Renovated Country Retreat, 11+ Acres by Evergreen Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover serenity nestled on 11 private acres, just 10 minutes from the charming village of Old Chatham. With 3 spacious ...
From $481 per night (USD)
Expedia
From $1014 per night (USD)
VRBO
Hudson Valley Lakefront Gem: 6 Bedrooms & Private Waterfront
Bedrooms:
3
Bathrooms:
6
Sleeps:
17
Just 2 hours from NYC or Boston, escape to a special retreat in the Hudson Valley! Swim, kayak, or paddle board on sceni ...
From $1014 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Sugar Shack - 300 square feet of pure sweetness.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A very Romantic-Private-Peaceful OASIS yet steps from quintessential Main Street lined with restaurants, brewery, shops, ...
From $274 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Sweet guest cottage perfectly located for exploring Columbia County, the Berkshires or simply lazing on the lawn with a ...
From $261 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Nordic Cabin: Light-Filled + Spacious w/Firepit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Nordic Cabin is a mid-century, Scandinavian-inspired home on 6 acres of woods—just 2 hrs from NYC! Bright, li ...
From $366 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
Upscale centrally air-conditioned lakefront cottage with 75 feet of lakefront property and a Landlord who lives to make ...
From $352 per night (USD)
VRBO
From $310 per night (USD)
VRBO
A 200 year old center hall colonial between the Berkshires and the Hudson River
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This property is located on an acre in a small village within easy walking distance of a gourmet country store, a tavern ...
From $310 per night (USD)
VRBO
From $1669 per night (USD)
VRBO
Spectacular All Seasons Retreat with Amazing Views
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Gorgeous 6000 square foot home with stunning views on 26 secluded acres. It's the perfect retreat for family gatherings ...
From $1669 per night (USD)
VRBO
$2,000 sq ft loft located \downtown\ with access to dining..shops...movie theater$
From $458 per night (USD)
VRBO
2,000 sq ft loft located \"downtown\" with access to dining..shops...movie theater
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on Main Street in “downtown” Chatham, chathamLoft75 is a 2,000 sq ft fully furnished second floor space that has ...
From $458 per night (USD)
VRBO
From $220 per night (USD)
VRBO
La Petite Maison, Chatham, NY
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Quiet, country setting one mile from downtown Chatham Village with private parking. Enjoy a very comfortable stay with m ...
From $220 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Heaven Can't Wait, On Beautiful Kinderhook Lake! 4TH OF JULY FIREWORKS ON LAKE!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Hello again repeat and new guests! Thank you for a very enjoyable 2024. All of you were great! We are looking forward to ...
From $228 per night (USD)
Expedia
From $1723 per night (USD)
VRBO
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Bedrooms:
5
Bathrooms:
8
Sleeps:
16
Bellavista Country Estate is a one-of-a kind, beautiful, special estate property. Privately located on 60 acres with poo ...
From $1723 per night (USD)
VRBO
From $1269 per night (USD)
Expedia
Amazing 5 Star Estate! FREE Day Passes to Wellness Center included w/ your stay!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
To see our nearly one hundred 5 star reviews on this property, please visit Listing # 387726. Please note that guest li ...
From $1269 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Chatham Cozy Country Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bright, two bedroom, one bathroom, open concept duplex (I live on the other side) with vaulted ceilings. Fully furnished ...
From $151 per night (USD)
VRBO
From $1192 per night (USD)
Expedia
Sprawling, Rustic Country Estate with Spring-Fed Swim Pond & Tennis Ct
Bedrooms:
6
Bathrooms:
8
Sleeps:
17
Huge, sprawling, 6,000 sq ft country estate situated on 10 acres of land which include both a 1/2 acre spring-fed swimmi ...
From $1192 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Camp Kinderhook Lake House
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This house is on a quiet cove on Kinderhook lake. It has been newly renovated within the past two years. And has a great ...
From $308 per night (USD)
VRBO
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Expedia
Renovated Chatham Home ~ Half Mi to Downtown!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Discover a quiet retreat in this stunning 4-bedroom, 2.5-bath vacation rental in Chatham, NY. Unwind and enjoy the charm ...
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Expedia
From $296 per night (USD)
VRBO
BLUSH: Boutique TINY home*private spa*walk to town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy in at this Romantic-Private-Peaceful OASIS & just steps from quintessential Main St. Indulgences abound in this one ...
From $296 per night (USD)
VRBO
From $152 per night (USD)
VRBO
Cozy Cottage in the Woods
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Cottage is an idyllic private one-bedroom cottage nestled in the woods. The place is equipped with a private queen-s ...
From $152 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Harmony House in Hudson Valley- Pet Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to the Harmony House, located within walking distance of the charming and historic Chatham town square. This coz ...
From $333 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Elegant Upstate Sanctuary on 20 Acres
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Mariposa Hill: a hidden gem in the Hudson Valley, approximately 2 hours from NYC. Set on 20 remarkable acres, ...
From $477 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Charming 1800s home with fenced in yard and bucolic farm views !
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Bucolic views of farmland in both the front and backyard, this charming home maintains its 1800s character while updated ...
From $326 per night (USD)
VRBO
From $286 per night (USD)
Expedia
HunnyHAUS: Deluxe TINY*private spa*walk to town
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Reserve this thoughtfully curated space just 2.5 hours from NYC or Boston. You'll fall in love with this Romantic-Privat ...
From $286 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Serenity on Stony Kill: 3BR Creek Front Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
The whole group will be comfortable in this bright, stunning, spacious, and unique rustic and renovated cottage on 10 ac ...
From $342 per night (USD)
VRBO
From $1597 per night (USD)
Expedia
Hudson Valley 10 Bedroom Compound with pond and tennis court
Bedrooms:
6
Bathrooms:
9
Sleeps:
25
Welcome to this welcoming house in Valatie. With 9 bedrooms featuring a mix of king and queen beds, this property offers ...
From $1597 per night (USD)
Expedia
From $1026 per night (USD)
VRBO
Spectacular 73 Acre, 6 Bedroom Estate, Large Heated Pool, 2 Gourmet Kitchens
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Spectacular house and property that lends itself to gracious and relaxing country living. This completely private 73 ac ...
From $1026 per night (USD)
VRBO
From $965 per night (USD)
VRBO
Haddock and Cotter a Charming Countryside Stay with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautifully restored 1834 farmhouse blends historic charm with chic, modern comfort. Perfect for hosting family and ...
From $965 per night (USD)
VRBO
From $501 per night (USD)
VRBO
Beautifully Designed 4BR Home with Heated Pool and HotTub
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This hilltop house sits secluded above Kinderhook Lake, offering a peaceful escape with elegant interiors and lots of na ...
From $501 per night (USD)
VRBO
From $408 per night (USD)
VRBO
Birds’ Nest Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Looking for a cozy summer getaway? Escape to Birds’ Nest Bungalow! This charming vintage 3-bedroom cottage is nestled al ...
From $408 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to max ...
From $392 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Farmhouse Retreat, Outdoor Dining/Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to The Olde Kinderhook House! A spacious, restored farmhouse on 3 private acres in the heart of the Hudson Vall ...
From $525 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Serene Modern Lakefront Escape: Kayaks, Fishing, Firepit, Private Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Lago, your perfect lakefront escape in the Hudson Valley! Enjoy stunning water views, a private dock, co ...
From $443 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Martin Van Buren lake Cottage 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Four saison cottage If you are into secluded Gem 💎 and a nature lover, then this place is for you ❤️ Back in the day ...
From $199 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Waterfront cottage on quiet lake with private beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterfront is waiting for you at this delightful 3-bedroom cottage With 1 king bed and 2 queen beds, this cozy retreat ...
From $405 per night (USD)
VRBO
From $682 per night (USD)
Expedia
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to the serene, secluded beauty of Hudson in the Berks, tucked away on a hill in East Chatham. This private retrea ...
From $682 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Cozy Chatham Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This charming house gives you a quiet sense of calm, while still being close enough to great places to dine, gain inspir ...
From $230 per night (USD)
VRBO
From $378 per night (USD)
VRBO
Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Bring your family and relax along the Lake - private launch - Open floor plan with a large rear deck to enjoy the sunshi ...
From $378 per night (USD)
VRBO
From $842 per night (USD)
VRBO
The Lakeshore House
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape to Your Private Lakeside Paradise! Looking for the perfect getaway? Welcome to the Lakeshore House, a breathtak ...
From $842 per night (USD)
VRBO
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Expedia
Four Seasons Luxury at 'Summerhill', Chatham, NY
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Listing description Enjoy our beautiful home perfectly located to experience the beauty of the Berkshires. Spend time on ...
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Expedia
From $746 per night (USD)
VRBO
4BR, 3.5BA Family House Great for Vacationing or Temporary Stays
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This well-appointed house is great not only for getaways and vacationing, but also for digital nomads, travel clinicians ...
From $746 per night (USD)
VRBO

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Town of Chatham Rentals

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Results: 43 Rentals