Book Cheap Hotels in Chatham

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Check prices in Chatham for tonight, Dec 6 - Dec 7
Dec 6 - Dec 7
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Check prices in Chatham for next weekend, Dec 12 - Dec 14
Dec 12 - Dec 14

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 $124 per night
CA $124
CA $154 total
Dec 7 - Dec 8
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
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 $111 per night
CA $111
CA $127 total
Dec 19 - Dec 20
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
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
Get rates
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
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 $128 per night
CA $128
CA $143 total
Dec 15 - Dec 16
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 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 $123 per night
CA $123
CA $138 total
Dec 14 - Dec 15
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
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 $152 per night
CA $152
CA $169 total
Dec 11 - Dec 12
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
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 $213 per night
CA $213
CA $299 total
Jan 5 - Jan 6, 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
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 $178 per night
CA $178
CA $226 total
Dec 7 - Dec 8
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
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
99 Miller Rd Castleton-on-Hudson NY
24.95 km from city centre
The price is CA $132 per night
CA $132
CA $147 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Castleton-on-Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Funplex Fun Park and Brookview Station Winery are located nearby.
Pool
Breakfast included
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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 $160 per night from Jan 5 to Jan 6
CA $160
CA $179 total
Jan 5 - Jan 6, 2026
includes taxes & fees
7.6/10 Good! (211 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
1,591 hotels
Lowest Price
CA $127
Highest Price
CA $299
Popular hotels
Vacation Village in the Berkshires, Comfort Inn Glenmont - Albany South, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Comfort Inn & Suites East Greenbush - Albany

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 $127 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 1,591 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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"All of the above "
A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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Areas of Chatham