Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

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Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 254 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

19–26 Oct

£99 per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 180 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

24–31 Aug

£134 per night

Guest favourite

Cottage in Kinderhook

4.98 out of 5 average rating, 171 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

7–14 Jul

£124 per night

Guest favourite

Home in Chatham

4.88 out of 5 average rating, 137 reviews

Country house on Indian Creek

Tucked away in a beautiful valley, this house is surrounded by farm hills and creeks. Located on 5 acres of grassland and 10 acres of woodland. Close to 3 ski mountains, 2 lakes, and tons of hiking and mountain biking trails. Very peaceful and spacious place to unwind. The center of town is 5 minutes away but the place feels miles away from everything. If you open my profile picture you will find my guidebook, which gives you a idea of some places to eat and attractions around the area.

1–8 May

£148 per night

Guest favourite

Home in Ghent

4.94 out of 5 average rating, 121 reviews

Blacksmith House, Ghent, NY

Built in 1790 as a blacksmith shop named “The Town Ax," Blacksmith House was rebuilt in the early 1990's and renovated by the present owners in 2017. The roughhewn beams of the original structure are exposed in every room. Approached by a grand stone staircase, set in a lilac-lined hamlet with plantings, surrounded by wildflowers, furnished with antiques and primitive Americana, Blacksmith House radiates tranquility and graciousness with its full-width front porch and classic proportions.

18–25 Apr

£199 per night

Guest favourite

Guest suite in Valatie

4.98 out of 5 average rating, 230 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

2–9 Sept

£79 per night

Guest favourite

Home in Chatham

4.9 out of 5 average rating, 144 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to fine dining & Main St pubs/pizza/movies/shopping. 12mi Hudson Amtrak (taxi, Uber avail). Walk to town park w/swim pond. 30mins Albany/Lenox. Keyless entry. Hosts a text away if needed. Smoke/Pet-free property. Check-in 4pm/-out 11a. 55" Sony Roku TV. Reliable high-speed WiFi. Stocked kitchen/full bath incl W/D. Private outdoor dining area w/propane bbq. 2 guests max preferred, a 3rd could be accommodated at extra charge.

20–27 Mar

£102 per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 306 reviews

HunnyHAUS: Deluxe TINY*private spa*walk to town

Reserve this thoughtfully curated space just 2.5 hours from NYC or Boston. You'll fall in love with this PRIVATE oasis in a canopy of trees overlooking the creek. Star gaze from your private hot tub (open year-round), sip cocktails around the fire. Walk to dinner OR cook in the well-equipped kitchen/outdoor grill. Immerse yourself in nature while enjoying the convenience of village life. Steps from restaurants, shops, theater, brewery.

7–14 Jul

£222 per night

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

27 Mar – 3 Apr

£72 per night

Guest favourite

Flat in Valatie

4.94 out of 5 average rating, 164 reviews

Holland House: Modern Rustic Guest Apartment

Thoughtfully designed two-bedroom apartment located above a former millinery shop built in 1880. Beautiful natural light. Mix of vintage and modern amenities, including two guest bedrooms, full kitchen and bath, high speed wifi, in-unit laundry and work desks. Private tree-shaded back porch overlooking Kinderhook Creek and Pachaquack Preserve. 20 minutes to Hudson. 30 minutes to Albany, the Berkshires and the Catskills.

4–11 Mar

£122 per night

Guest favourite

Cabin in Chatham

4.98 out of 5 average rating, 102 reviews

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

24–31 May

£319 per night

Guest favourite

Apartment in Hudson

4.94 out of 5 average rating, 140 reviews

Harmony Valley Home, bright & inviting 2-BR escape

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries breweries Musuems Hiking trails Empire State Rail Trail Conservation Areas

8–15 Nov

£121 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chatham's top sights

Our Daily Bread Deli66 locals recommend

Chatham Brewing114 locals recommend

Chatham Grill21 locals recommend

Columbia County Fair Grounds7 locals recommend

Yianni's20 locals recommend

The People's Pub54 locals recommend

Other great holiday rentals in Chatham

Guest favourite

Home in Ghent

4.96 out of 5 average rating, 213 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

7–14 Sept

£198 per night

Guest favourite

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

20–27 May

£259 per night

Guest favourite

Cabin in Ghent

4.99 out of 5 average rating, 180 reviews

Cozy chalet w/ fireplace near Hudson & hiking

27 Sept – 4 Oct

£269 per night

Guest favourite

Flat in Chatham

5.0 out of 5 average rating, 8 reviews

Private Victorian Guest Suite - Chatham Village

9–16 Sept

£104 per night

Guest favourite

Home in Chatham

4.98 out of 5 average rating, 96 reviews

Hilltop studio apartment on 100 acres near village

2–9 May

£99 per night

Guest favourite

Flat in Chatham

4.91 out of 5 average rating, 34 reviews

Neat 2 bedroom in the village private access

13–20 Oct

£118 per night

Guest favourite

Flat in East Chatham

4.91 out of 5 average rating, 44 reviews

Bennett Abode

19–26 Nov

£86 per night

Guest favourite

Flat in Canaan

4.98 out of 5 average rating, 84 reviews

Mountain View Getaway

23–30 Dec

£94 per night

Show all

Quick stats about holiday rentals in Chatham

Total rentals	10 properties
Local attractions	Our Daily Bread Deli, Chatham Brewing and Chatham Grill
Popular amenities	Kitchen, Wifi and Pool
Wifi availability	10 properties include access to wifi
Total number of reviews	1K reviews
Nightly prices starting at	£80 before taxes and fees

Holiday rentals in Chatham

Top-rated holiday rentals in Chatham

Flat in Copake Falls

Tiny home in Chatham

Cottage in Kinderhook

Home in Chatham

Home in Ghent

Guest suite in Valatie

Home in Chatham

Tiny home in Chatham

Guest suite in Austerlitz

Flat in Valatie

Cabin in Chatham

Apartment in Hudson

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chatham holiday rentals

Stay near Chatham's top sights

Other great holiday rentals in Chatham

Home in Ghent

Tiny home in Ghent

Cabin in Ghent

Flat in Chatham

Home in Chatham

Flat in Chatham

Flat in East Chatham

Flat in Canaan

Quick stats about holiday rentals in Chatham

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore