North Chatham Vacation Rentals

Our Favorite Vacation Rentals in Chatham

  • Beauty in the Berkshires
     6br Home/Apartment
    HolidayLettings
    From
    $1,374
  • Total Privacy! Tanglewood Retreat With Berkshire Views!
     5br Home/Apartment
    HolidayLettings
    From
    $902
  • Relax Like Royalty in Your Own Castle!
     2br Home/Apartment
    HolidayLettings
    From
    $342
  • Chalet near 4 ski resorts with hot tub
     3br Home/Apartment
    HolidayLettings
    From
    $514
  • Hillhouse Log Cabin
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $487
  • 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

  • Secluded Landscaped Grounds 1/2 Hour from Skiing
    Excellent3br Home/Apartment
    Airbnb
    From
    $311
  • Berkshire Winter and Ski Mountain Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $972
  • Chic Converted Barn
    Excellent3br Home/Apartment
    Airbnb
    From
    $220
  • Haddock Hill Guest House
     3br Home/Apartment
    Airbnb
    From
    $662

Chatham Vacation Rentals with Wi-Fi

  • Charming Secluded Country Getaway
    Excellent4br Home/Apartment
    Airbnb
    From
    $464
  • Home Sweet Home in a Best Place to Live Locale
    Excellent2br Home/Apartment
    Airbnb
    From
    $203
  • Beautiful Lake/Mountain Views. Bright Sunlit Home.
    Excellent4br Home/Apartment
    Airbnb
    From
    $407
  • Close to Hudson and the Berkshires
    Excellent4br Home/Apartment
    Airbnb
    From
    $295

Chatham Pet-Friendly Vacation Rentals

  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $386
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $460
  • NEW! Lakefront Berkshires House w/Deck, Dock +Boat
     4br Home/Apartment
    HolidayLettings
    From
    $519
  • Retrograss Farm Apartment
    Excellent2br Home/Apartment
    Airbnb
    From
    $130

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
54° -11°
5
60° -5°
3
67°
1
74° 19°
5
83° 36°
4
85° 39°
5
90° 51°
4
86° 43°
2
85° 34°
3
73° 29°
8
66° 11°
4
53°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Chatham. The warmest months in Chatham are June and May, when temperatures reach 90 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in Chatham is March with 8.3 inches of rain, while the driest month is October with 1.25 inches of rain.

What Expert Travelers Think

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    My Anasa
    My AnasaMy Anasa
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

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    Jeff CampbellMiddle Class Dad
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

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