Chatham Vacation Homes

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Featured Vacation Homes in Chatham

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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.

Hotel Options in Chatham

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $108 nightly
    The price is $121 total per night from Nov 16 to Nov 17
    $121 total
    Nov 16 - Nov 17
    Total with taxes and fees
    Country Inn & Suites by Radisson, Downtown Albany New York

    Country Inn & Suites by Radisson, Downtown Albany New York

    300 Broadway Albany NY
    $101 nightly
    The price is $116 total per night from Nov 22 to Nov 23
    $116 total
    Nov 22 - Nov 23
    Total with taxes and fees
    8.2/10 Very Good! (1,263 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $107 nightly
    The price is $119 total per night from Dec 14 to Dec 15
    $119 total
    Dec 14 - Dec 15
    Total with taxes and fees

Chatham Vacation Homes

Book vacation homes in Chatham
Next time you take a group getaway top Chatham, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Chatham vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Chatham vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Chatham; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Chatham rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Chatham is sure to be a winner.

Chatham Vacation Homes essential information

Accommodation
449 Vacation Homes
Lowest Price
$116
Highest Price
$343
Popular accommodation
Modern Luxurious Cabin, Catskills - The Tiny Nook, Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room, Leaf-Peeper Paradise in the Berkshires , Catskill Cottage Walk to Downtown & River Views, Hilltop Escape with Views & Hot Tub, RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes, Modern Designer Chalet on 5.5 Private Acres Near Tanglewood, Incredible Estate: Pool, Pond, Gym, Arcade, Trails & More: Book Summer 2027 Now!, Great Barrington, Cabin Sleeps 14, Walk To Town