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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.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $309, price is now $260 per person
$260
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Save 100% on your flight
Price was $505, price is now $391 per person
$391
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $375, price is now $295 per person
$295
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Wilderness Trails and Vermont Institiute of Natural Science are located nearby.
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $2,005, price is now $1,591 per person
$1,591
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this vacation home in Plymouth. Enjoy free parking and laundry facilities. Popular attractions Okemo Mountain Resort and Camp Plymouth State Park are located nearby.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Save 100% on your flight
Price was $463, price is now $375 per person
$375
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,166, price is now $944 per person
$944
per person
Jan 5 - Jan 9
found 21 hours 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.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,241, price is now $1,046 per person
$1,046
per person
Feb 20 - Feb 22
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $680, price is now $588 per person
$588
per person
Feb 13 - Feb 15
found 4 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and 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 Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $375, price is now $295 per person
$295
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Save 100% on your flight
Price was $505, price is now $391 per person
$391
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $2,005, price is now $1,591 per person
$1,591
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Save 100% on your flight
Price was $463, price is now $375 per person
$375
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip 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.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,370, price is now $1,210 per person
$1,210
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Rutland (RUT)
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $2,052, price is now $1,805 per person
$1,805
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $2,095, price is now $1,844 per person
$1,844
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,044, price is now $1,811 per person
$1,811
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Rutland (RUT)

Top Flight Deals

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

JetBlue Airways
Thu, Feb 12 - Mon, Feb 16
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$249 Roundtrip, found 16 hours ago
$249
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Feb 12 from John F. Kennedy Intl. to Lebanon Municipal, returning Mon, Feb 16, priced at $249 found 16 hours ago
American Airlines
Mon, Feb 9 - Mon, Feb 9
LGA
LaGuardia
LEB
Lebanon Municipal
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Feb 9 from LaGuardia to Lebanon Municipal, returning Mon, Feb 9, priced at $304 found 1 day ago
JetBlue Airways
Wed, Dec 17 - Wed, Dec 24
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Dec 17 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 24, priced at $344 found 1 day ago
United
Fri, Dec 12 - Tue, Dec 16
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$364 Roundtrip, found 4 days ago
$364
Roundtrip
found 4 days ago
Select United flight, departing Fri, Dec 12 from Newark Liberty Intl. Airport to Rutland Southern Vermont Regional, returning Tue, Dec 16, priced at $364 found 4 days ago