Book Cheap Hotels in Chatham

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Check prices in Chatham for tonight, Dec 29 - Dec 30
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Most frequently booked Chatham hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free cancellation
Reserve now, pay when you stay
33.49 km from city centre
The price is CA $142 per night
CA $142
CA $174 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
31.65 km from city centre
The price is CA $176 per night
CA $176
CA $250 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park are located nearby.
Kitchen
Pet-friendly
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Free cancellation
32.39 km from city centre
The price is CA $108 per night
CA $108
CA $123 total
Jan 22 - Jan 23, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Glenmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Crossgates Mall and Historic Cherry Hill are located nearby.
Pool
Breakfast included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
27.24 km from city centre
The price is CA $138 per night
CA $138
CA $154 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
29.4 km from city centre
The price is CA $121 per night
CA $121
CA $135 total
Jan 3 - Jan 4, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free cancellation
Reserve now, pay when you stay
24.99 km from city centre
The price is CA $185 per night
CA $185
CA $268 total
Jan 26 - Jan 27, 2026
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Pool
Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
27.73 km from city centre
The price is CA $135 per night
CA $135
CA $181 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Hot tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
26.52 km from city centre
The price is CA $173 per night
CA $173
CA $193 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kennedy Park and Pleasant Valley Wilderness Sanctuary are located nearby.
Pet-friendly
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Free cancellation
28.28 km from city centre
The price is CA $175 per night
CA $175
CA $222 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Berkshire Theatre Festival and Schantz Galleries are located nearby.
Pool
Air conditioning
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See all available properties in Chatham
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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.

Top family friendly Chatham hotel deals

Chatham Travel Lodge

Chatham Travel Lodge

598 NY-295 Old Chatham NY
The price is CA $159 per night from Dec 30 to Dec 31
CA $159
CA $178 total
Dec 30 - Dec 31
includes taxes & fees
7.6/10 Good! (212 reviews)

Top hotels in Chatham for Extended Stay

Suite 4 - Quiet and private accommodations in a country setting.

Suite 4 - Quiet and private accommodations in a country setting.

Spencertown NY
10/10 Exceptional! (3 reviews)
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.

Chatham hotels essential information

Accommodation
1,588 hotels
Lowest Price
CA $123
Highest Price
CA $268
Popular hotels
Vacation Village in the Berkshires, Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy, Comfort Inn Glenmont - Albany South, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Red Lion Inn, Berkshire Mountain Lodge, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

What are the top kid-friendly hotels in Chatham?
Family getaways are where wonderful memories are made, but traveling with young ones can be demanding. These kid-friendly Chatham hotels offer perks that aim to keep young and old alike relaxed and happy: You'll be well looked after at The Honeydew: Cozy*hot tub*fire pit*walk to dinner. It comes with a firepit, a fireplace and a knack for making families feel at home. Alternatively, spend your nights in Chatham at Charming Farm House on 460 Acre Working Farm. Take advantage of a deck, animal viewing activities and more here.
Where can I find cheap hotels in Chatham?
At Travelocity you'll find really nice hotels in Chatham at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chatham rather than in Chatham. We may find you even better rates, too.
How do I find the best Chatham hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chatham then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chatham?
The cheapest hotel in Chatham is CA $123 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chatham?
There are 1,588 hotels in Chatham on Travelocity.
What are the best hotels in Chatham?
Chatham has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chatham for you!
When is the best time to visit Chatham?
If you want the joy of a fun-filled trip in peak season, visit Chatham during February, March and May. If you'd prefer the peace of off-season, book a stay during quieter months, such as June, September and October.
When is the cheapest time to stay in Chatham?
Based on historic data is usually the cheapest month to visit Chatham. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chatham?
There are multiple hotels in Chatham that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chatham. We have plenty of kid-friendly hotels in Chatham to choose from on Travelocity!
Why book a hotel in Chatham through Travelocity?
Because we have the top hotels in Chatham! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chatham on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chatham hotel reviews by fellow wanderers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5 out of 5
Posted 14 hours ago
Travelocity Verified Review
"The stay was wonderful! The hotel is VERY clean, comfortable, and the staff are so lovely! I really enjoyed staying here. You're treated like family (in a good way). It is well situated for restaurants and skiing. I will definitely return."
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham

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Areas of Chatham