Search Deals onRutland Vacation Packages
Rutland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast
Price was $587, price is now $510 per person
$510
per person
Jan 6 - Jan 10
found 2 hours ago
Roundtrip 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.
Clean, comfortable, convenient. We couldn't stay for breakfast.
Reviewed on Nov 8, 2026
Lake Bomoseen Lodge
Price was $743, price is now $591 per person
$591
per person
Dec 17 - Dec 21
found 1 day 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.
Beautiful and comfortable lodge with a wonderful lake view and stunning scenery, staff was very helpfull !
Reviewed on Nov 12, 2026
Mountain Green Resort
Price was $1,686, price is now $1,342 per person
$1,342
per person
Jan 6 - Jan 10
found 2 hours 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
Price was $1,563, price is now $1,254 per person
$1,254
per person
Jan 6 - Jan 10
found 2 hours 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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $647, price is now $550 per person
$550
per person
Dec 17 - Dec 21
found 1 day 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 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
Killington Haus
Price was $670, price is now $598 per person
$598
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this guesthouse in Killington. Enjoy free WiFi, free parking, and a restaurant. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Days Inn by Wyndham Rutland/Killington Area
Price was $1,049, price is now $936 per person
$936
per person
Dec 16 - Dec 21
found 1 day 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.
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
Castle Hill Resort And Spa
Price was $1,636, price is now $1,506 per person
$1,506
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
I promise, especially if you’re staying in the condo buildings you will love it
Reviewed on Sep 23, 2026
Rutland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Rutland Vacation Packages 5-7 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.
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$555 Roundtrip, found 4 days ago
$555
Roundtrip
found 4 days ago
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$575 Roundtrip, found 4 days ago
$575
Roundtrip
found 4 days ago
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$581 Roundtrip, found 4 days ago
$581
Roundtrip
found 4 days ago
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$594 Roundtrip, found 4 days ago
$594
Roundtrip
found 4 days ago
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