Chatham Cottages

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Cottages in Chatham

Rose Cottage

Located in Leeds, this cottage is in a rural location, a 5-minute drive from Catskill Golf Club and 5 minutes from Thomas Cole National Historic Site.

Loblolly Cottage - Enchanting Retreat set among towering pines.

Located in Germantown, this cottage is on a lake, a 2-minute drive from Hudson River and 7 minutes from The Clermont Mansion.

Free WiFi

Air conditioning

Quiet rustic cottage with shared lake access

With a stay at this cottage in Great Barrington, you'll be on a lake, just steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.

Washer

Dryer

Charming Cottage in the Heart of Catskill & Pet Friendly

A stay at this cottage places you in the heart of Catskill, within a 15-minute walk of Greene County Council on the Arts and Dutchman’s Landing.

Kitchen

Washer

Cozy Berkshire cottage with fireplace.

With a stay at this cottage in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Guido's Marketplace.

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

With a stay at this cottage in Great Barrington, you'll be steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.

Kitchen

Washer

Welcome to the Red Bridge Cottage!

Located in Valatie, this cottage is in a rural location, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.

Charming Cottage in Private Lake Community (Pet-Friendly!)

Located in Athens, this cottage is on a lake, a 1-minute drive from Sleepy Hollow Lake and 7 minutes from Hudson River.

Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!

A stay at this cottage places you in the heart of Hudson, steps from Max and Lillian Katzman Theater and 15 minutes by foot from Hudson Opera House.

The Blue Elm - A Historic Berkshire Cottage

$413

includes taxes & fees

$370 per night

Dec 2 - Dec 3

Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.

Cozy cottage with pool, walking distance to lake

When you stay at this cottage in Averill Park, you'll be on a lake and 14 minutes by car from Pineridge Cross Country Ski Center.

Fun Getaway Lakehouse in the Hudson Valley

Located in Copake Lake, this cottage is on a lake, a 1-minute drive from Copake Lake and 7 minutes from Mosquito Island.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.