Book Cheap Hotels in Chatham

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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 $129 per night
CA $129
CA $159 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star 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.
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 $131 per night
CA $131
CA $178 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star 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 Tanglewood Music Center and Guido's Marketplace are located nearby.
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 $123 per night
CA $123
CA $137 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3.5-star 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 Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
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
29.4 km from city centre
The price is CA $145 per night
CA $145
CA $162 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star 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.
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
27.92 km from city centre
The price is CA $149 per night
CA $149
CA $167 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
31.65 km from city centre
Get rates
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.
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
Reserve now, pay when you stay
28.28 km from city centre
The price is CA $163 per night
CA $163
CA $202 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3.5-star 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 Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning
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 $186 per night
CA $186
CA $271 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
26.9 km from city centre
The price is CA $118 per night
CA $118
CA $132 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
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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 $163 per night from Oct 30 to Oct 31
CA $163
CA $182 total
Oct 30 - Oct 31
includes taxes & fees
7.6/10 Good! (202 reviews)

Top hotels in Chatham for Extended Stay

Bentley Brook the perfect home base for exploring nearby Berkshire County

Bentley Brook the perfect home base for exploring nearby Berkshire County

Hancock
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
1,590 hotels
Lowest Price
CA $132
Highest Price
CA $271
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, Berkshires Untold, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Postcard Cabins Eastern Catskills, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, Quality Inn

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 $132 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 1,590 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"Clean and great pool and hot tub facilities "
A verified traveller stayed at Vacation Village in the Berkshires
Vacation Village in the Berkshires

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Areas of Chatham