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Pittsfield Vacation Packages

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Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $635, price is now $523 per person
$523
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pico Mountain at Killington Ski Resort and Killington Resort are located nearby.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,163, price is now $884 per person
$884
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $900, price is now $714 per person
$714
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,012, price is now $817 per person
$817
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,141, price is now $928 per person
$928
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,467, price is now $1,197 per person
$1,197
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $1,048, price is now $873 per person
$873
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Summit Lodge

Summit Lodge

3 out of 5
Price was $800, price is now $691 per person
$691
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this inn in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $900, price is now $714 per person
$714
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,163, price is now $884 per person
$884
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,012, price is now $817 per person
$817
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,141, price is now $928 per person
$928
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)

Pittsfield Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $1,048, price is now $873 per person
$873
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,467, price is now $1,197 per person
$1,197
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $3,434, price is now $2,992 per person
$2,992
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
Price was $2,382, price is now $2,134 per person
$2,134
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)

Top Flight Deals

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

Delta
Sun, Feb 8 - Tue, Feb 10
EWR
Newark Liberty Intl. Airport
LEB
Lebanon Municipal
$300 Roundtrip, found 16 hours ago
$300
Roundtrip
found 16 hours ago
Select Delta flight, departing Sun, Feb 8 from Newark Liberty Intl. Airport to Lebanon Municipal, returning Tue, Feb 10, priced at $300 found 16 hours ago
JetBlue Airways
Tue, Feb 10 - Tue, Feb 17
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$301 Roundtrip, found 3 hours ago
$301
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Feb 10 from John F. Kennedy Intl. to Lebanon Municipal, returning Tue, Feb 17, priced at $301 found 3 hours ago
American Airlines
Mon, Feb 9 - Mon, Feb 9
LGA
LaGuardia
LEB
Lebanon Municipal
$302 Roundtrip, found 20 hours ago
$302
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Mon, Feb 9 from LaGuardia to Lebanon Municipal, returning Mon, Feb 9, priced at $302 found 20 hours ago
JetBlue Airways
Fri, Feb 13 - Tue, Feb 17
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Feb 13 from John F. Kennedy Intl. to Lebanon Municipal, returning Tue, Feb 17, priced at $309 found 2 days ago