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Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chatham vacation rentals

Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ￥43,388
￥55,209 total
includes taxes & fees
Aug 3 - Aug 4
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

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 ￥43,388
￥53,742 total
includes taxes & fees
Aug 19 - Aug 20
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥37,658
￥62,165 total
includes taxes & fees
Jul 29 - Jul 30
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

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, (4 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 ￥49,283
￥108,743 total
includes taxes & fees
Aug 25 - Aug 26
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (159 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is ￥22,695
￥25,416 total
includes taxes & fees
Aug 6 - Aug 7
Micosta Leisure Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,029 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is ￥19,681
￥25,642 total
includes taxes & fees
Aug 27 - Aug 28
Berkshire Mountain Lodge
1 bedroom, WiFi (free), bed sheets

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is ￥22,922
￥33,077 total
includes taxes & fees
Jul 29 - Jul 30
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
House (3 Bedrooms) | Front of property

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is ￥49,640
￥96,902 total
includes taxes & fees
Aug 5 - Aug 6
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (262 reviews)
"It was great!"
United States
India
The price is ￥29,144
￥38,549 total
includes taxes & fees
Aug 27 - Aug 28
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,482 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is ￥17,865
￥21,751 total
includes taxes & fees
Aug 11 - Aug 12
Vacation Village in the Berkshires
Pool

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (8 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is ￥16,062
￥21,655 total
includes taxes & fees
Jul 29 - Jul 30
All comforts of home
Terrace/patio

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
Athens
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful property that was clean. Hosts left information about surrounding area and restaurants- we definitely felt welcomed when we arrived. Beautiful area with lots to do! Would stay here again"
United States
Sarah M.
The price is ￥40,441
￥97,963 total
includes taxes & fees
Aug 5 - Aug 6
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ￥53,049
￥95,907 total
includes taxes & fees
Aug 9 - Aug 10
Gorgeous Mountain Views Retreat: Family & Nature
Pool

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
The price is ￥37,003
￥67,483 total
includes taxes & fees
Jul 29 - Jul 30
Hudson NY’S Country Serenity Guest Suite.
Outdoor dining

NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥47,318
￥95,258 total
includes taxes & fees
Jul 29 - Jul 30
NEW RENO Historic Creamery in Berkshires w/hot tub
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥17,388
￥23,143 total
includes taxes & fees
Aug 3 - Aug 4
All the comforts of home
Terrace/patio

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥30,618
￥59,415 total
includes taxes & fees
Aug 3 - Aug 4
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
House (3 Bedrooms) | Interior

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 ￥36,676
￥90,733 total
includes taxes & fees
Jul 29 - Jul 30
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥39,073
￥59,383 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Riverside Berkshires Retreat
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 Chatham Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Loved the voew from our balcony of the lake. Breakfasts were great. Well located. A good place to see the Berkshires from."
Judith 5-night trip
Posted 2 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near 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 5 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.

How many vacation rentals are there in Chatham?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Kinderhook Lake. The Mac-Haydn Theatre and Hudson Chatham Winery are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.