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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.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $759, price is now $677 per person
$677
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Very clean, large room. Full kitchen.

Reviewed on Oct 28, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,221, price is now $939 per person
$939
per person
Dec 2 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,437, price is now $1,117 per person
$1,117
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions T-Bar and Rope Tow are located nearby.

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,067, price is now $923 per person
$923
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop 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 helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
Nice place good breakfast

Reviewed on Oct 27, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,038, price is now $903 per person
$903
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
I love staying here!

Reviewed on Oct 27, 2026

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $941, price is now $820 per person
$820
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop 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.

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,350, price is now $1,181 per person
$1,181
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free WiFi, free parking, and a conference center. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Our room was large and comfortable, with a large, well-supplied bathroom. The fellow at the front desk was friendly and helpful. It feels like a very nice rural country inn. There isn't a lot else there, as there aren't 24-hour onsite staff or a fitness room or many other lobby amenities. I wouldn't hesitate to come back.

Reviewed on Oct 15, 2026

Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $806, price is now $716 per person
$716
per person
Dec 2 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.

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 $662, price is now $580 per person
$580
per person
Dec 17 - Dec 21
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,221, price is now $939 per person
$939
per person
Dec 2 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $972, price is now $847 per person
$847
per person
Dec 17 - Dec 21
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $806, price is now $716 per person
$716
per person
Dec 2 - Dec 6
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)

Pittsfield Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,038, price is now $903 per person
$903
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,437, price is now $1,117 per person
$1,117
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,814, price is now $1,467 per person
$1,467
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,067, price is now $923 per person
$923
per person
Dec 16 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)

Top Flight Deals

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

JetBlue Airways
Wed, Nov 18 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$424 Roundtrip, found 8 hours ago
$424
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Sat, Dec 5, priced at $424 found 8 hours ago
JetBlue Airways
Wed, Nov 18 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$434 Roundtrip, just found
$434
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Sat, Dec 5, priced at $434 just found
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$445 Roundtrip, found 6 hours ago
$445
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $445 found 6 hours ago
JetBlue Airways
Tue, Nov 17 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$455 Roundtrip, found 14 hours ago
$455
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Sun, Dec 6, priced at $455 found 14 hours ago