Chatham Vacation Homes

Aerial scene of Chatham, Ontario, Canada

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chatham holiday homes

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

Chatham

Jim S.

HK$2,667 total

includes taxes & fees

7 Jun - 8 Jun

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

Old Chatham

Terri E.

HK$4,422 total

includes taxes & fees

10 Jun - 11 Jun

All the comforts of home

Hudson

Olivia C.

HK$1,107 total

includes taxes & fees

8 Jun - 9 Jun

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill

Saul

HK$2,674 total

includes taxes & fees

10 Jun - 11 Jun

Catskill Stay w/ Deck & Fire Pit

Catskill

Cha R.

HK$3,485 total

includes taxes & fees

7 Jun - 8 Jun

stylish Berkshires Retreat

Lee

HK$2,867 total

includes taxes & fees

8 Jun - 9 Jun

Cozy Riverside Berkshires Retreat

Great Barrington

Cristine C.

HK$2,497 total

includes taxes & fees

7 Jun - 8 Jun

Near Tanglewood: Historic Summer Retreat

New Lebanon

Karen H.

HK$3,009 total

includes taxes & fees

7 Jun - 8 Jun

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

Country Inn & Suites by Radisson, Downtown Albany New York

4/10 Poor

"Too much noise from traffic at night not peaceful sleep. They closed the breakfast before the time . About this property breakfast time is Full breakfast included Served daily from 6:30 AM - 10:00 AM We were there 9:35 and it was closed. I tell to the receptionist that’s the time online. She was not helpful at all. Very disappointed"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"I went on a solo cabin trip and it was so relaxed and peaceful! The condition of the cabin was better than I expected it to be and the staff were super friendly and accommodating. Definitely plan to go again next year! The cabin had so many supplies from cooking material, mini fridge (no freezer portion), lighters, books, games, stereo! I will say if you're able to rent a car, please do so. It was easy to Uber from New York City to the property, but to get an Uber back into the city was very hard. I ended up calling a taxi service. Lesson learned lol"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Wonderful hidden gem of a little hotel. Right on lake laurel we had a beautiful lake view. Rooms were very clean. Decent breakfast. Well Located and close to Lee downtown main st, the Lennox Main Street and Stockbridge as well. Looking forward to returning"

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

Find out more about Chatham