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Old Chatham Vacation Packages

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Old Chatham Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $613, price is now $485 per person
$485
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this family-friendly guesthouse in Lenox. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,227, price is now $811 per person
$811
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,328, price is now $904 per person
$904
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail.

Reviewed on Sep 12, 2026

The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $976, price is now $667 per person
$667
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely.

Reviewed on Sep 4, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $3,106, price is now $2,182 per person
$2,182
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $806, price is now $572 per person
$572
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this ski 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.
The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat.

Reviewed on Sep 9, 2026

Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Save 100% on your flight
Price was $886, price is now $668 per person
$668
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Kingston. Enjoy free WiFi, room service, and free bicycles on site. Popular attractions Kingston Point Beach and Trolley Museum of New York are located nearby.
Stayed for one night and it was a great place for an anniversary getaway. The views and grounds were beautiful. Our cottage was cozy and perfect. We were able to charge our EV vehicle overnight which was very helpful. The sauna experience was nice and the Pavillion restaurant was excellent.

Reviewed on Aug 28, 2026

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $853, price is now $675 per person
$675
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Oakdale Beach and Hudson Area Library are located nearby.

Old Chatham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $976, price is now $667 per person
$667
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,328, price is now $904 per person
$904
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,453, price is now $1,036 per person
$1,036
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $1,803, price is now $1,409 per person
$1,409
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Old Chatham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $806, price is now $572 per person
$572
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,440, price is now $931 per person
$931
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,757, price is now $1,168 per person
$1,168
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $3,106, price is now $2,182 per person
$2,182
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Thu, Oct 15 - Sun, Oct 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 16 hours ago
$187
Roundtrip
found 16 hours ago
Select Allegiant Air flight, departing Thu, Oct 15 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Oct 18, priced at $187 found 16 hours ago
Bargain Flight
Sat, Sep 26 - Tue, Sep 29
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$260 Roundtrip, found 7 hours ago
$260
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Sat, Sep 26 from Charlotte-Douglas Intl. to Albany Intl., returning Tue, Sep 29, priced at $260 found 7 hours ago
Bargain Flight
Tue, Oct 20 - Sat, Oct 24
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$293 Roundtrip, found 2 hours ago
$293
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sat, Oct 24, priced at $293 found 2 hours ago
Bargain Flight
Tue, Oct 20 - Sat, Oct 24
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$320 Roundtrip, found 17 hours ago
$320
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Dallas-Fort Worth Intl. to Albany Intl., returning Sat, Oct 24, priced at $320 found 17 hours ago