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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
$122 nightly
The price is $136
Dec 6 - Dec 7
Total with taxes and fees
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
$113 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
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
$106 nightly
The price is $118
Dec 7 - Dec 8
Total with taxes and fees
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.
$533 nightly
The price is $597
Nov 16 - Nov 17
Total with taxes and fees
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.
$279 nightly
The price is $315
Nov 16 - Nov 17
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

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.
$280 nightly
The price is $316
Nov 10 - Nov 11
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
A camping setup with a metal chair and a table by a river in a forest.

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.
$291 nightly
The price is $326
Nov 8 - Nov 9
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A patio with stone flooring, wicker chairs, and a red umbrella. A lake with a dock and a small boat is visible in the background.

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
$605 nightly
The price is $671
Nov 8 - Nov 9
Total with taxes and fees
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
$270 nightly
The price is $292
Dec 4 - Dec 5
Total with taxes and fees
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.
$765 nightly
The price is $849
Nov 9 - Nov 10
Total with taxes and fees
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
$508 nightly
The price is $563
Nov 8 - Nov 9
Total with taxes and fees
A stunning, modern Lodge with rustic charm at June Farms!
A stone bridge with a wooden door, surrounded by a forest.

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 traveler
$580 nightly
The price is $644
Dec 2 - Dec 3
Total with taxes and fees
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
$529 nightly
The price is $587
Nov 8 - Nov 9
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A mobile home with a covered patio area, surrounded by trees.

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
$420 nightly
The price is $466
Nov 9 - Nov 10
Total with taxes and fees
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
$145 nightly
The price is $160
Nov 7 - Nov 8
Total with taxes and fees
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
$110 nightly
The price is $123
Nov 9 - Nov 10
Total with taxes and fees
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.
$194 nightly
The price is $196
Nov 8 - Nov 9
Total with taxes and fees
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.
$232 nightly
The price is $250
Nov 7 - Nov 8
Total with taxes and fees
★ 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.
$309 nightly
The price is $346
Nov 9 - Nov 10
Total with taxes and fees
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.
$557 nightly
The price is $623
Nov 8 - Nov 9
Total with taxes and fees
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."
Holly 3-night trip
Posted 8 hours ago
Berkshire Mountain Lodge

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit North Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $118 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.