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Rutland Vacation Packages

A forest with autumn foliage and a distant view of a town.

Rutland Flight + Hotel Packages

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

Days Inn by Wyndham Rutland/Killington Area

$617

per person

Dec 16 - Dec 19

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.

Spacious updated rooms. LOVE the vinyl vs. carpeted floors in the rooms, much cleaner. Breakfast needs more healthy options... low fat or fat free yogurts/milk, lower sugar options, eggs. Overall, a great overnight stay.

Reviewed on Nov 7, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

$961

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

We were so happy with everything Clean linens Well stocked kitchen Great grounds Helpful staff One minor issue--heat in halls too high, like uncomfortably warm We had windows open at times in November

Reviewed on Nov 9, 2026

The Suites at Killington Center

$987

per person

Dec 16 - Dec 19

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 Killington School for Tennis are located nearby.

Mountain Green Resort

$1,187

per person

Dec 16 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) 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

My Place Hotel-Randolph VT

$713

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Golden Stage Inn B&B

$756

per person

Dec 16 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Rutland (RUT)

Stay at this B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.

Just love this place. Stayed twice. Julie and Mike are such lovely hosts. So down to earth and make you so welcome. Lots of wee special touches and a lovely varied breakfast. Lots of fantastic travel advice too.

Reviewed on Oct 20, 2026

Emrose Luxury Cabins

$1,000

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Rutland (RUT)

Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Stephen A Douglas Birthplace and Judith Reilly Gallery are located nearby.

Lake Bomoseen Lodge

$802

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Beautiful and comfortable lodge with a wonderful lake view and stunning scenery, staff was very helpfull !

Reviewed on Nov 12, 2026

Rutland Vacation Packages 3-4 Night Stays

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