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Pittsfield Vacation Packages

Build your package with 2 more options

Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $553, price is now $499 per person
$499
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
Four Columns Inn

Four Columns Inn

4 out of 5
Price was $586, price is now $525 per person
$525
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this B&B in Newfane. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Moore Free Library and Rock River Preserve are located nearby.
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,381, price is now $1,266 per person
$1,266
per person
Jul 26 - Jul 30
found 1 hour ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this luxury guesthouse in Bolton Landing. Enjoy free WiFi, a full-service spa, and room service. Popular attractions Lake George and Adirondack Extreme Adventure Course are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $745, price is now $689 per person
$689
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Black Dog Sports are located nearby.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $708, price is now $663 per person
$663
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Killington School for Tennis are located nearby.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $730, price is now $690 per person
$690
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
Price was $740, price is now $701 per person
$701
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $843, price is now $799 per person
$799
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $553, price is now $499 per person
$499
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,381, price is now $1,266 per person
$1,266
per person
Jul 26 - Jul 30
found 1 hour ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)

Top Flight Deals

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

JetBlue Airways
Mon, Sep 21 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 3 days ago
$502
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Sep 21 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $502 found 3 days ago
United
Fri, Sep 11 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$509 Roundtrip, found 3 days ago
$509
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $509 found 3 days ago
JetBlue Airways
Mon, Sep 21 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$512 Roundtrip, found 5 days ago
$512
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Sep 21 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $512 found 5 days ago
United
Wed, Sep 23 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$745 Roundtrip, found 4 days ago
$745
Roundtrip
found 4 days ago
Select United flight, departing Wed, Sep 23 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $745 found 4 days ago