North Chatham Vacation Rentals

Our Favorite Vacation Rentals in Chatham

  • Tentrr - Hillsdale Hideaway
     Country House
    Booking.com
    From
    $133
  • Beauty in the Berkshires
     6br Home/Apartment
    HolidayLettings
    From
    $1,374
  • Total Privacy! Tanglewood Retreat With Berkshire Views!
     5br Home/Apartment
    HolidayLettings
    From
    $988
  • Relax Like Royalty in Your Own Castle!
     2br Home/Apartment
    HolidayLettings
    From
    $342
  • Hudson Valley Cottage
    ExcellentCottage
    HolidayLettings
    From
    $200
  • Berkshire Country Estate - The Library Suite
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $172
  • mile hill b and b
     2br Home/Apartment
    HolidayLettings
    From
    $240
  • RiverSong Suite In The Berkshires
    ExcellentHome/Apartment
    HolidayLettings
    From
    $256

Check prices for these upcoming dates

Chatham Vacation Rentals with a Pool

  • spencertown farm house
    Excellent4br Home/Apartment
    Airbnb
    From
    $848
  • Low Meadow Farm, Hudson River Valley NY
    Excellent4br Farm Stay
    Airbnb
    From
    $667
  • Berkshire Winter and Ski Mountain Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,136
  • Haddock Hill Guest House
     3br Home/Apartment
    Airbnb
    From
    $757

Chatham Vacation Rentals with Wi-Fi

  • Home Sweet Home in a Best Place to Live Locale
    Excellent2br Home/Apartment
    Airbnb
    From
    $203
  • Close to Hudson and the Berkshires
    Excellent4br Home/Apartment
    Airbnb
    From
    $295
  • Retrograss Farm Apartment
    Excellent2br Home/Apartment
    Airbnb
    From
    $131
  • Angel Hill House
    Excellent2br Home/Apartment
    Airbnb
    From
    $270

Chatham Pet-Friendly Vacation Rentals

  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $457
  • Newly renovated guesthouse on 52 acres!
    ExcellentHome/Apartment
    Airbnb
    From
    $263
  • Shady Mountain Getaway w Private Swimming Pond
    Good3br Home/Apartment
    Airbnb
    From
    $246
  • Charming, private and quiet guest bungalow
    ExcellentHome/Apartment
    Airbnb
    From
    $161

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
Most availability
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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 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 Weather in Chatham

Rainy days
64°
6
59°
4
61° -10°
5
73° -3°
4
55°
2
67° 18°
4
86° 40°
3
91° 42°
3
93° 46°
5
90° 51°
8
89° 40°
7
79° 27°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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 December, when temperatures drop to -10 ˚F. The wettest month in Chatham is May with 8.25 inches of rain, while the driest month is October with 2.35 inches of rain.

What Expert Travelers Think

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