North Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for North Chatham vacation rentals

Indoor pool

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,830 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $112
CA $141 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (195 reviews)
"Great stay"
United States
George
The price is CA $138
CA $154 total
includes taxes & fees
Nov 9 - Nov 10
Micosta Leisure Inn
Exterior

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $107
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A modern building with a wooden deck and a door.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is CA $362
CA $823 total
includes taxes & fees
Nov 17 - Nov 18
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

5. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
The price is CA $362
CA $444 total
includes taxes & fees
Nov 16 - Nov 17
Sugar Shack - 300 square feet of pure sweetness.
A hot tub with a tray of champagne glasses, a bottle, and a candle.

6. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is CA $362
CA $444 total
includes taxes & fees
Nov 10 - Nov 11
BLUSH: Boutique TINY home*private spa*walk to town
Exterior

7. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is CA $279
CA $460 total
includes taxes & fees
Nov 8 - Nov 9
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden cabin room with a bed, a hanging light fixture, and a window with curtains.

8. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
United States
KenD
The price is CA $415
CA $963 total
includes taxes & fees
Nov 9 - Nov 10
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
A cabin with a triangular window, wooden walls, and a bed with pillows.

9. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is CA $394
CA $425 total
includes taxes & fees
Nov 27 - Nov 28
Gather Greene
A spacious living area with a high ceiling, wooden beams, a chandelier, a fireplace, a television, and a kitchen in the background.

10. Private Family Cabin on 3.5 Acres • Hot Tub • Mini Golf • Water Access

Private Family Cabin on 3.5 Acres • Hot Tub • Mini Golf • Water Access
Castleton-on-Hudson
10.0 out of 10, Exceptional, (13 reviews)
"Great property for our family get together. Clean. Well decorated. Private. Fun game room."
United States
Aileen N.
The price is CA $639
CA $1,192 total
includes taxes & fees
Nov 9 - Nov 10
Private Family Cabin on 3.5 Acres • Hot Tub • Mini Golf • Water Access
A rustic cabin interior with a stone fireplace, wooden beams, a bar area, and a cozy seating arrangement.

11. A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (5 reviews)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
The price is CA $453
CA $848 total
includes taxes & fees
Nov 8 - Nov 9
A stunning, modern Lodge with rustic charm at June Farms!
A bedroom with a stone wall, a bed with a blue blanket, a wooden nightstand with a lamp, and a small chair.

12. WOW! A spectacular Hobbit House in the forest at June Farms!

WOW! A spectacular Hobbit House in the forest at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"Good atmosphere and the details were great!"
United States
Anonymous traveller
The price is CA $543
CA $899 total
includes taxes & fees
Dec 6 - Dec 7
WOW! A spectacular Hobbit House in the forest at June Farms!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

13. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is CA $355
CA $821 total
includes taxes & fees
Nov 8 - Nov 9
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A modern kitchen with white cabinets, a wooden countertop, and a built-in oven.

14. Luxury, modern AIRSTREAM at June Farms!

Luxury, modern AIRSTREAM at June Farms!
West Sand Lake
9.8 out of 10, Exceptional, (7 reviews)
"We’ve stayed at several of the various cabins at June Farms. This one, like the others, is unique and fantastic. Would absolutely stay again!"
United States
StephenS
The price is CA $340
CA $655 total
includes taxes & fees
Nov 9 - Nov 10
Luxury, modern AIRSTREAM at June Farms!
A wooden cabin with a porch, a door, and a window.

15. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (20 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is CA $157
CA $224 total
includes taxes & fees
Nov 8 - Nov 9
Taborton Harvest Boulder Pines Cabin in the woods
A wooden deck with a staircase leading to a covered porch area.

16. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is CA $137
CA $172 total
includes taxes & fees
Nov 9 - Nov 10
All comforts of home
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

17. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is CA $98
CA $270 total
includes taxes & fees
Nov 7 - Nov 8
NEW RENO - Chalet-style farm loft near Tanglewood
A hallway with a welcome sign, a door on the left, and a window at the end.

18. ★ 2 BEDROOM / 1 BATH TRENDY Apt ★ Downtown Albany

★ 2 BEDROOM / 1 BATH TRENDY Apt ★ Downtown Albany
Downtown Albany
8.6 out of 10, Excellent, (39 reviews)
"This property was very convenient to the downtown location of the MVP arena. We did enjoy our stay."
United States
Amanda W.
The price is CA $195
CA $349 total
includes taxes & fees
Nov 7 - Nov 8
★ 2 BEDROOM / 1 BATH TRENDY Apt ★ Downtown Albany
A backyard with a fire pit, wooden deck, and string lights.

19. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is CA $261
CA $488 total
includes taxes & fees
Nov 9 - Nov 10
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A cozy living room with a sofa, a fireplace, and large windows.

20. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is CA $534
CA $913 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Barn Near Hudson With New Private Sauna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top North Chatham Hotel Reviews

A hotel with a covered entrance, stone facade, and arched windows.
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
Castleton-on-Hudson

10/10 Excellent

Clean room. Plenty of parking. Convenient breakfast
Canada
Mateo
Reviewed October 7, 2026
Comfort Inn & Suites East Greenbush - Albany

Find out more about North Chatham

Everything you need to know about North Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the North Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

North Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Chatham vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Chatham vacation rentals we have selected for you start as low as CA $97 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on North Chatham rentals

At Expedia, we put the best North Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top North Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in North Chatham?

Yes, there are vacation rentals close to the most popular sights in North Chatham, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in North Chatham?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of North Chatham is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What’s there to see and do in North Chatham?

Explore the area and family-friendly sights such as USS Slater, or get out into nature at a spot like Kinderhook Lake. Martin Van Buren National Historic Site and Art Omi International Arts Center - Fields Sculpture Park are a couple of places you'll find in the larger area.

What’s a vacation rental in North Chatham like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in North Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.