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North Chatham Vacation Rentals

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Our Favorite Vacation Rentals in Chatham

  • Beauty in the Berkshires
    Beauty in the Berkshires
     
    HolidayLettingsFrom $1374
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  • Relax Like Royalty in Your Own Castle!
    Relax Like Royalty in Your Own Castle!
     
    HolidayLettingsFrom $342
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  • Hudson Valley Cottage
    Hudson Valley Cottage
    Excellent
    HolidayLettingsFrom $200
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  • Berkshire Country Estate - Rose Suite
    Berkshire Country Estate - Rose Suite
     
    HolidayLettingsFrom $195
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  • Relaxing Victorian Farmhouse
    Relaxing Victorian Farmhouse
     
    HolidayLettingsFrom $281
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  • mile hill b and b
    mile hill b and b
     
    HolidayLettingsFrom $240
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  • RiverSong Suite In The Berkshires
    RiverSong Suite In The Berkshires
    Excellent
    HolidayLettingsFrom $242
    View Deal
  • Beautifully decorated & immaculate log chalet
    Beautifully decorated & immaculate log chalet
    Excellent
    HolidayLettingsFrom $258
    View Deal
See all 46 vacation rentals in Chatham

Chatham Vacation Rentals with a Pool

  • Secluded Pool and Garden Oasis
    Secluded Pool and Garden Oasis
     
    AirbnbFrom $454
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  • Country Getaway Tiny House in Woods w/Pool nearby.
    Country Getaway Tiny House in Woods w/Pool nearby.
    Excellent
    AirbnbFrom $224
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  • Berkshires Rustic Retreat (but near everything!)
    Berkshires Rustic Retreat (but near everything!)
    Excellent
    AirbnbFrom $162
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  • Bigger Views: Heated pool, hot tub and MUCH MORE!
    Bigger Views: Heated pool, hot tub and MUCH MORE!
    Excellent
    AirbnbFrom $2783
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See all vacation rentals in Chatham with a pool

Chatham Vacation Rentals with Wi-Fi

  • Home Sweet Home in a Best Place to Live Locale
    Home Sweet Home in a Best Place to Live Locale
    Excellent
    AirbnbFrom $235
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  • Close to Hudson and the Berkshires
    Close to Hudson and the Berkshires
    Excellent
    AirbnbFrom $279
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  • Hilltop studio apartment on 100 acres near village
    Hilltop studio apartment on 100 acres near village
    Excellent
    AirbnbFrom $127
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  • Angel Hill House
    Angel Hill House
    Excellent
    AirbnbFrom $307
    View Deal
See all vacation rentals in Chatham with WiFis

Chatham Pet-Friendly Vacation Rentals

  • To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
    To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
    Excellent
    HolidayLettingsFrom $515
    View Deal
  • Upstate getaway on 52 acres!
    Upstate getaway on 52 acres!
    Excellent
    AirbnbFrom $260
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  • Shady Mountain Getaway w Private Swimming Pond
    Shady Mountain Getaway w Private Swimming Pond
    Good
    AirbnbFrom $244
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  • Country Retreat
    Country Retreat
     
    AirbnbFrom $358
    View Deal
See all vacation rentals 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

86º 40º
2.56
91º 42º
3.42
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
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
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.

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