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A lake surrounded by autumn-colored trees and a rocky shoreline.

Pittsfield
Vermont
United States of America
North America
Hotwire.com

Pittsfield Flight + Hotel Packages

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

My Place Hotel-Randolph VT

2 out of 5

Price was $911, price is now $729 per person

$729

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip non-stop 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.

Needed to be told about turning on ice maker - missed no breakfast

Reviewed on Oct 10, 2026

Mountain Green Resort

4 out of 5

Save 100% on your flight

Price was $5,634, price is now $4,036 per person

$4,036

per person

Dec 24 - Dec 31

found 1 hour ago

Roundtrip non-stop flight included

Orlando (MCO) 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 Black Dog Sports are located nearby.

I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Suites at Killington Center

3.5 out of 5

Save 100% on your flight

Price was $4,880, price is now $3,515 per person

$3,515

per person

Dec 24 - Dec 31

found 1 hour ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Pointe at Castle Hill Resort

3.5 out of 5

Price was $2,237, price is now $1,804 per person

$1,804

per person

Dec 24 - Dec 31

found 1 hour ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Nice facility. Clean and convenient.

Reviewed on Oct 10, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5

Price was $1,739, price is now $1,448 per person

$1,448

per person

Dec 24 - Dec 31

found 1 hour ago

Roundtrip non-stop flight included

Orlando (MCO) 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 Mount Ascutney and Mt Ascutney State Park are located nearby.

70 year old couple got upgraded to a suite because of overbooking of the ground floor 1 bedroom unit. However the suite included 32 steps with no elevators. Nice fire pit in the evening. No breakfast or lunch options on property.

Reviewed on Oct 10, 2026

The Landgrove

3.5 out of 5

Price was $1,105, price is now $938 per person

$938

per person

Dec 20 - Dec 23

found 24 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Rutland (RUT)

Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bromley Mountain Ski Resort and Hapgood Pond are located nearby.

We arrived late, there was someone there to greet us. I had left a personal item, they were kind enough to call and mail it to us.

Reviewed on Oct 3, 2026

Bentley House Bed and Breakfast

2 out of 5

Price was $1,208, price is now $1,027 per person

$1,027

per person

Dec 24 - Dec 31

found 1 hour 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.

Very unique house with lovely furnishings. Owners were very helpful and breakfast was delicious.

Reviewed on Oct 9, 2026

Greenbrier Inn

2 out of 5

Price was $2,111, price is now $1,806 per person

$1,806

per person

Dec 24 - Dec 31

found 1 hour ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

I would highly recommend this inn. Its small

Reviewed on Oct 10, 2026

Pittsfield Vacation Packages 3-4 Night Stays

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

Lake Bomoseen Lodge

3.5 out of 5

Price was $489, price is now $420 per person

$420

per person

Dec 11 - Dec 14

found 10 hours ago

Roundtrip flight included

New York (NYC) to Rutland (RUT)

The Landgrove

3.5 out of 5

Price was $1,105, price is now $938 per person

$938

per person

Dec 20 - Dec 23

found 24 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Rutland (RUT)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5

Price was $977, price is now $866 per person

$866

per person

Dec 14 - Dec 17

found 1 day ago

Roundtrip non-stop flight included

San Antonio (SAT) to Rutland (RUT)