Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Putney Inn
Price was $627, price is now $569 per person
$569
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yellow Barn and Next Stage Arts are located nearby.
Clean, quiet, easy access from highway.
Reviewed on Aug 22, 2026
Greenbrier Inn
Price was $873, price is now $715 per person
$715
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Gifford Woods State Park are located nearby.
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on Aug 3, 2026
The Mountain Inn at Killington
Price was $952, price is now $803 per person
$803
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Bentley House Bed and Breakfast
Price was $764, price is now $670 per person
$670
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Owners are very nice and friendly. Property /room is clean. Breakfast is ok. Will recommend to stay here.
Reviewed on Aug 18, 2026
Lake Bomoseen Lodge
Price was $895, price is now $793 per person
$793
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
It’s all about the views!
Reviewed on Aug 22, 2026
North Star Lodge and Resort
Price was $910, price is now $809 per person
$809
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Clean rooms!! The heated pool was amazing and so dreamy at night! The bar lounge was exemplary! Definitely will be staying there again!
Reviewed on Aug 22, 2026
The Landgrove
Price was $1,115, price is now $995 per person
$995
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hapgood Pond and Wild Wings Ski Touring Center are located nearby.
Emrose Luxury Cabins
Price was $812, price is now $742 per person
$742
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
The property is beautiful loved the heated pool and outdoor activities .
Reviewed on Aug 19, 2026
Pittsfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Sep 23 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 6 days ago
$514
Roundtrip
found 6 days ago
Tue, Sep 22 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$521 Roundtrip, found 6 days ago
$521
Roundtrip
found 6 days ago
Mon, Sep 14 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$521 Roundtrip, found 1 day ago
$521
Roundtrip
found 1 day ago
Sun, Sep 20 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$734 Roundtrip, found 1 day ago
$734
Roundtrip
found 1 day ago
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