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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 Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $581, price is now $534 per person
$534
per person
Apr 17 - Apr 19
found 8 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,475, price is now $1,280 per person
$1,280
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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 Engel House

The Engel House

3 out of 5
Price was $1,075, price is now $941 per person
$941
per person
Apr 6 - Apr 12
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this B&B in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Pond and Honora Winery are located nearby.
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $2,357, price is now $2,073 per person
$2,073
per person
Apr 1 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) 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.
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
Price was $937, price is now $826 per person
$826
per person
Apr 1 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this ski hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pico Mountain at Killington Ski Resort and Green Mountain Rock Climbing Center are located nearby.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,081, price is now $960 per person
$960
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Price was $1,526, price is now $1,377 per person
$1,377
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this apartment in Killington. Enjoy free parking, a full-service spa, and a fitness center. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $784, price is now $713 per person
$713
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

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

Cortina Inn

3 out of 5
Price was $565, price is now $547 per person
$547
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Price was $1,526, price is now $1,377 per person
$1,377
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $724, price is now $688 per person
$688
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)

Pittsfield Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
Price was $937, price is now $826 per person
$826
per person
Apr 1 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,475, price is now $1,280 per person
$1,280
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
The Engel House

The Engel House

3 out of 5
Price was $1,075, price is now $941 per person
$941
per person
Apr 6 - Apr 12
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $2,357, price is now $2,073 per person
$2,073
per person
Apr 1 - Apr 6
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)