Search Deals onChittenden Vacation Packages
Chittenden Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT
Price was $620, price is now $465 per person
$465
per person
Nov 11 - Nov 18
found 15 hours ago
Roundtrip flight included
New York (NYC) 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.
Lake Bomoseen Lodge
Save 100% on your flight
Price was $815, price is now $586 per person
$586
per person
Nov 11 - Nov 18
found 15 hours ago
Roundtrip flight included
New York (NYC) 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.
Wonderful lake view. Snacks and coffee were useful in the morning. Fire pit and free canoe use rounded out the trip!
Reviewed on Aug 26, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $894, price is now $690 per person
$690
per person
Nov 11 - Nov 18
found 15 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.
Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night.
Reviewed on Aug 15, 2026
Bentley House Bed and Breakfast
Price was $834, price is now $648 per person
$648
per person
Nov 11 - Nov 18
found 15 hours ago
Roundtrip flight included
New York (NYC) 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 clean, very friendly, good breakfast, very nice Victorian style house
Reviewed on Aug 25, 2026
Greenbrier Inn
Price was $1,207, price is now $957 per person
$957
per person
Sep 27 - Oct 2
found 3 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on Aug 3, 2026
Chateau Rooms
Price was $1,006, price is now $806 per person
$806
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this luxury guesthouse in Bolton Landing. Enjoy free WiFi, a full-service spa, and room service. Popular attractions Lake George and Adirondack Extreme Adventure Course are located nearby.
Shabby chic room, lovely bedding and comfy.
Nice big new shower. But I've decided that I cannot live without a TV!
Reviewed on Aug 20, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $741, price is now $595 per person
$595
per person
Nov 11 - Nov 18
found 15 hours ago
Roundtrip 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 Mount Ascutney and Mt Ascutney State Park are located nearby.
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
The Mountain Inn at Killington
Price was $1,091, price is now $888 per person
$888
per person
Nov 11 - Nov 18
found 4 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Chittenden Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chittenden Vacation Packages 5-7 Night Stays
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