Deals on vacations and trips to Old Chatham

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The Dewey

The Dewey

3.5 out of 5
Price was $855, price is now $681 per person
$681
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,183, price is now $839 per person
$839
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,012, price is now $783 per person
$783
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $1,235, price is now $969 per person
$969
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $859, price is now $684 per person
$684
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Top Old Chatham hotels deals

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham NY
Get rates
This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. A garden, a library, and laundry facilities are also on offer.
Pool
Kitchen
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
$126 nightly
The price is $141 total per night
$141 total
Jan 19 - Jan 20
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
82 MONTGOMERY STREET Albany NY
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Breakfast included
Pet friendly
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
$98 nightly
The price is $109 total per night
$109 total
Jan 23 - Jan 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
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
$93 nightly
The price is $103 total per night
$103 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Free Cancellation
$81 nightly
The price is $93 total per night
$93 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
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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.

Popular places to visit

Shaker Museum and Library

You can spend time browsing the exhibits at Shaker Museum and Library in Old Chatham. While you're in the area, wander around the gardens.

Shaker Museum and Library

Frequently asked questions

How much are vacation packages to Old Chatham?
Treat yourself to a memorable travel experience in Old Chatham with a vacation package starting at just $681. Organizing your flights, tours and hotels with Travelocity is so easy. On top of that, our packages will leave you with more savings in your pocket for loads of fun times.
How long should my Old Chatham vacation be?
If you're looking for some guidance, most visitors spend approximately 2 nights vacationing in Old Chatham. But to discover the true spirit of this place, stay a few extra days. You'll be able to check off more attractions and really take in the local culture.
Where can I get the best vacation package deals for Old Chatham?
With as many as 400 partner airlines and 1,000,000 hotels around the world, it's hard to go past Travelocity. Scroll through our impressive range and create your dream Old Chatham package deal. Don't you love it when trip planning is that easy?
Why should I book my Old Chatham vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you can rest easy knowing you'll always get the best deal available.
Will I save money on my Old Chatham car rental if I bundle it with hotels and flights?
Combining your flight, car and hotel into an Old Chatham vacation package is the best way to score the best deal. Plus, having your own wheels gives you freedom to get to all those big sights you're hoping to explore. Sitting 120 mi away from Old Chatham, Times Square is one attraction that should have a place on your itinerary. Fill up the tank and make a day trip of it.
Which airport is best for Old Chatham?
One top option is Bradley Intl. Airport (BDL). From here, you'll need to travel northwest for about 55 mi to reach inner Old Chatham. Another convenient choice is Albany Intl. Airport (ALB), 25 mi away from central Old Chatham.
Where should I stay when visiting Old Chatham?
The Chatham Travel Lodge is the number one choice of many visitors. Book now to avoid missing out.

Photos of local treasures

Browse Old Chatham vacation photos for more inspiration