North Chatham Vacation Rentals

Our Favorite Vacation Rentals in Chatham

  • Tentrr - Powell Farm
     Country House
    Booking.com
    From
    $115
  • Beauty in the Berkshires
     6br Home/Apartment
    HolidayLettings
    From
    $1,374
  • Tentrr - Hillsdale Hideaway
     Country House
    Booking.com
    From
    $115
  • 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
  • Hillhouse Log Cabin
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $487
  • Hudson Valley Cottage
    ExcellentCottage
    HolidayLettings
    From
    $200
  • Berkshire Country Estate - The Library Suite
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $172

Check prices for these upcoming dates

Chatham Vacation Rentals with a Pool

  • spencertown farm house
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,074
  • Secluded Pool and Garden Oasis
    Excellent3br Home/Apartment
    Airbnb
    From
    $410
  • Berkshire Winter and Ski Mountain Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,074
  • Country Getaway Tiny House in Woods w/Pool nearby.
    ExcellentHome/Apartment
    Airbnb
    From
    $226

Chatham Vacation Rentals with Wi-Fi

  • 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
    $281
  • Getaway in Farm Country
    ExcellentFarm Stay
    Airbnb
    From
    $86

Chatham Pet-Friendly Vacation Rentals

  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $342
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $304
  • NEW! Lakefront Berkshires House w/Deck, Dock +Boat
     4br Home/Apartment
    HolidayLettings
    From
    $332
  • Shady Mountain Getaway w Private Swimming Pond
    Good3br Home/Apartment
    Airbnb
    From
    $234

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
89 º40
7
79 º27
3
64 º0
6
59 º9
4
61 º-10
5
73 º-3
4
55 º7
2
67 º18
4
86 º40
3
91 º42
3
93 º46
5
90 º51
8
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

Destinations near Chatham

  • New York18,240 Properties
  • Brooklyn10,467 Properties
  • Niagara Falls4,610 Properties
  • Queens2,938 Properties
  • Lake Placid1,528 Properties
  • Ithaca1,514 Properties
  • Montauk1,402 Properties
  • Rochester879 Properties
  • Sag Harbor857 Properties
  • Lake George Village812 Properties
  • Amagansett763 Properties
  • Hampton Bays697 Properties
  • Southampton638 Properties
  • Springs628 Properties
  • Albany620 Properties
  • Hudson586 Properties
  • Woodstock558 Properties
  • Ellicottville558 Properties
  • Cooperstown556 Properties
  • Village of East Hampton552 Properties
  • Lake George544 Properties
  • Saugerties542 Properties
  • Hunter534 Properties
  • Canandaigua463 Properties
  • Windham434 Properties
  • Ocean Beach432 Properties
  • Saranac Lake428 Properties
  • Geneva410 Properties
  • Bridgehampton392 Properties
  • Kingston386 Properties
  • Beacon383 Properties
  • Chautauqua364 Properties
  • Watkins Glen363 Properties
  • Wilmington360 Properties
  • Staten Island353 Properties
  • Penn Yan343 Properties
  • Cherry Grove338 Properties
  • Syracuse337 Properties
  • Noyack330 Properties
  • Hammondsport324 Properties
  • Buffalo315 Properties
  • New Paltz311 Properties
  • East Quogue306 Properties
  • Yonkers301 Properties
  • Alexandria Bay298 Properties
  • Watermill291 Properties
  • Southold286 Properties
  • Greenport286 Properties
  • Chestertown282 Properties
  • Cortland273 Properties
  • Bolton Landing273 Properties
  • Long Beach271 Properties
  • Wainscott270 Properties
  • Queensbury270 Properties
  • Warrensburg264 Properties
  • Plattsburgh259 Properties
  • Binghamton251 Properties
  • White Plains241 Properties
  • Shelter Island237 Properties
  • Auburn236 Properties
  • Old Forge234 Properties
  • Rhinebeck229 Properties
  • Westhampton Beach221 Properties
  • Poughkeepsie215 Properties
  • Amherst214 Properties
  • North Creek211 Properties
  • Catskill203 Properties
  • Skaneateles203 Properties
  • Westhampton202 Properties
  • Trumansburg200 Properties
  • Saratoga Springs188 Properties
  • Pulaski184 Properties
  • Schroon Lake181 Properties
  • Dundee170 Properties
  • Clayton161 Properties
  • Quogue146 Properties
  • Fishkill138 Properties
  • Newburgh138 Properties
  • Fire Island118 Properties
  • Tupper Lake105 Properties
  • Mount Vernon101 Properties
  • Fleischmanns90 Properties
  • Diamond Point73 Properties
  • Millbrook73 Properties
  • Riverhead65 Properties
  • Ellenville53 Properties
  • City of Gloversville47 Properties
  • Port Jefferson41 Properties
  • Findley Lake37 Properties
  • Croton-on-Hudson33 Properties
  • Adirondack30 Properties
  • Sodus Point25 Properties
  • Washingtonville20 Properties
  • Star Lake8 Properties