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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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $666, price is now $499 per person
$499
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this golf aparthotel 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.
I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay.

Reviewed on Oct 3, 2026

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $755, price is now $537 per person
$537
per person
Dec 22 - Dec 27
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.
Wonderful resort

Reviewed on Sep 29, 2026

Hotel On North

Hotel On North

3.5 out of 5
Price was $743, price is now $545 per person
$545
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.
Delightful place with charm and warmth and character. I would love to come back.

Reviewed on Oct 2, 2026

Hyatt House Schenectady / Mohawk Harbor

Hyatt House Schenectady / Mohawk Harbor

3 out of 5
Price was $945, price is now $697 per person
$697
per person
Nov 29 - Dec 3
found 3 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Rivers Casino & Resort and Schenectady City Hall are located nearby.
Amazing service and very clean property.

Reviewed on Sep 29, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,296, price is now $962 per person
$962
per person
Nov 5 - Nov 9
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.

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $698, price is now $521 per person
$521
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this family-friendly aparthotel 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.

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $6,445, price is now $5,075 per person
$5,075
per person
Nov 29 - Dec 3
found 4 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $6,458, price is now $5,088 per person
$5,088
per person
Nov 29 - Dec 3
found 4 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.

Old Chatham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt House Schenectady / Mohawk Harbor

Hyatt House Schenectady / Mohawk Harbor

3 out of 5
Nothside
Price was $945, price is now $697 per person
$697
per person
Nov 29 - Dec 3
found 3 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,296, price is now $962 per person
$962
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $6,445, price is now $5,075 per person
$5,075
per person
Nov 29 - Dec 3
found 4 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $6,458, price is now $5,088 per person
$5,088
per person
Nov 29 - Dec 3
found 4 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)

Old Chatham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $666, price is now $499 per person
$499
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $755, price is now $537 per person
$537
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Hotel On North

Hotel On North

3.5 out of 5
Price was $743, price is now $545 per person
$545
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $698, price is now $521 per person
$521
per person
Dec 22 - Dec 27
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 29 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$210 Roundtrip, found 7 hours ago
$210
Roundtrip
found 7 hours ago
Select Allegiant Air flight, departing Thu, Oct 29 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sat, Nov 14, priced at $210 found 7 hours ago
Bargain Flight
Sat, Oct 31 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Oct 31 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Fri, Nov 13, priced at $275 found 2 days ago
Bargain Flight
Tue, Oct 20 - Tue, Nov 3
TPA
Tampa Intl.
ALB
Albany Intl.
$299 Roundtrip, found 6 hours ago
$299
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Tampa Intl. to Albany Intl., returning Tue, Nov 3, priced at $299 found 6 hours ago
Bargain Flight
Tue, Oct 20 - Sat, Oct 24
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Oct 20 from Dallas-Fort Worth Intl. to Albany Intl., returning Sat, Oct 24, priced at $304 found 2 days ago