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North Chatham Vacation Rentals

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Our Favorite Vacation Rentals in Chatham

  • Relax Like Royalty in Your Own Castle!
    Relax Like Royalty in Your Own Castle!
     2br Home/Apartment
    HolidayLettingsFrom $342
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  • Berkshire Country Estate - Rose Suite
    Berkshire Country Estate - Rose Suite
     2br Country House
    HolidayLettingsFrom $195
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  • Relaxing Victorian Farmhouse
    Relaxing Victorian Farmhouse
     3br Farmhouse
    HolidayLettingsFrom $269
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  • mile hill b and b
    mile hill b and b
     2br Home/Apartment
    HolidayLettingsFrom $240
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  • RiverSong Suite In The Berkshires
    RiverSong Suite In The Berkshires
    Excellent1br Home/Apartment
    HolidayLettingsFrom $256
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  • Overnight at Althouse -Higgins
    Overnight at Althouse -Higgins
    Excellent2br Home/Apartment
    HolidayLettingsFrom $229
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  • Charming Secluded Country Getaway
    Charming Secluded Country Getaway
    Excellent4br Home/Apartment
    AirbnbFrom $464
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  • Comfortable Camping in the Woods
    Comfortable Camping in the Woods
    ExcellentOther
    AirbnbFrom $73
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See all 46 deals in Chatham

Chatham Vacation Rentals with a Pool

  • Charming 1800 Eyebrow Colonial
    Charming 1800 Eyebrow Colonial
    Good3br Home/Apartment
    AirbnbFrom $559
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  • Berkshires Rustic Retreat (close to everything!)
    Berkshires Rustic Retreat (close to everything!)
    Excellent1br Home/Apartment
    AirbnbFrom $158
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  • Idyllic Berkshires Retreat With Pond Views & Pool
    Idyllic Berkshires Retreat With Pond Views & Pool
    Excellent2br Home/Apartment
    AirbnbFrom $452
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  • The Home in Malden Bridge, Columbia County, NY
    The Home in Malden Bridge, Columbia County, NY
    Excellent2br Home/Apartment
    AirbnbFrom $345
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See all deals in Chatham with a pool

Chatham Vacation Rentals with Wi-Fi

  • Historic 3BR cottage for perfect family weekends
    Historic 3BR cottage for perfect family weekends
    Excellent3br Cottage
    AirbnbFrom $244
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  • Chatham NY Cottage
    Chatham NY Cottage
    Excellent3br Home/Apartment
    AirbnbFrom $243
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  • Forest Cabin
    Forest Cabin
    Excellent1br Cabin
    AirbnbFrom $264
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  • Charming Ghent Getaway, minutes from Hudson!
    Charming Ghent Getaway, minutes from Hudson!
    Excellent1br Home/Apartment
    AirbnbFrom $96
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See all deals in Chatham with WiFis

Chatham Pet-Friendly Vacation Rentals

  • Upstate getaway on 52 acres!
    Upstate getaway on 52 acres!
    Excellent1br Home/Apartment
    AirbnbFrom $240
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  • Chatham Rail House
    Chatham Rail House
    Good2br Home/Apartment
    AirbnbFrom $254
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  • Private Village Studio
    Private Village Studio
     2br Home/Apartment
    AirbnbFrom $142
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  • Berkshires Best -Hudson, NY to Great Barrington
    Berkshires Best -Hudson, NY to Great Barrington
     3br Home/Apartment
    AirbnbFrom $283
    View Deal
See all deals in Chatham that allow pets

Chatham Travel Guide

A quaint and pretty rural village in upstate New York, Chatham has a distinct small town appeal with its eclectic stores, restaurants, and surrounding countryside.

Things to Do in Chatham

Get your bearings with a walking tour in the historic center of Chatham. Between the 1850s and1950s, hundreds of trains traveling on the Boston & Albany line stopped in Chatham. The tour will take tourists past various historic and beautiful buildings such as Union Station, the clock tower, the theater, and the library.Explore what Chatham has to offer in the way of arts and culture with a fun live dance, music, fine art galleries, and film. There are plenty of unique stores and some great places to dine in town too.

Best Time to Visit Chatham

It's always nice to visit upstate New York in late summer or early fall, when the weather is still lovely and the colors are beginning to change.

Price and Availability in Chatham

Most expensive
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The most expensive month to stay in a vacation rental in Chatham is in June, while the cheapest month is in April. The most popular time to book a vacation rental in Chatham is in the high season in July. Chatham has its low season in April, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Chatham tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Chatham tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Chatham

93º 46º
4.68
90º 51º
8.25
89º 40º
6.89
79º 27º
2.84
64º 0º
6.39
59º 9º
3.94
61º -10º
4.66
73º -3º
4.09
55º 7º
2.35
67º 18º
3.63
86º 40º
2.56
91º 42º
3.42
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
This climate histogram shows you the weather patterns in Chatham. The hottest month in Chatham is June, when temperatures peak at 93 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Chatham is August with 8.25 inches of rain, while the driest month is March with 2.35 inches of rain.

What Expert Travelers Think

Destinations near Chatham