Shoreham Vacations from $904
Book a Hotel + Flight or Car together to unlock savings
The Latest Shoreham Vacation Packages
- Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Oct 7 - Oct 10Holiday Inn Club Vacations Mount Ascutney Resort by IHG + Flight
Brownsville3 nights3.0 star property9.0/10 - Wonderful (862 reviews)Roundtrip • New York (EWR) - Rutland (RUT)EWR - RUT • 1 stop RUT - EWR • 1 stop$1,074$904found 1 day agoper traveler - The Mountain Inn at Killington
Sep 8 - Sep 14The Mountain Inn at Killington + Flight
Killington6 nights2.5 star property9.2/10 - Wonderful (1,005 reviews)Roundtrip • Chicago (CHI) - Rutland (RUT)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,307$1,098found 1 day agoper traveler - Days Inn by Wyndham Rutland/Killington Area
Sep 8 - Sep 14Days Inn by Wyndham Rutland/Killington Area + Flight
Rutland6 nights2.5 star property6.8/10 - (1,004 reviews)"Just a quick trip up for a work event, easy to check in, pool is open late so everyone an relax even after a late check in. So many restaurants to choose from!"Reviewed August 2, 2026Roundtrip • Chicago (CHI) - Rutland (RUT)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,155$978found 1 day agoper traveler - Greenbrier Inn
Sep 8 - Sep 14Greenbrier Inn + Flight
Killington6 nights2.0 star property9.4/10 - Exceptional (686 reviews)"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 August 3, 2026Roundtrip • Chicago (CHI) - Rutland (RUT)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,201$1,021found 1 day agoper traveler - Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Sep 8 - Sep 14Ski in & out Spruce Glen Townhomes on Great Eastern Trail + Flight
Killington6 nights3.0 star property9.0/10 - Wonderful (64 reviews)"We completely. Enjoyed every second of this property We are now looking for. Homes. Near by! We. Would have rented this areas. /Condo. Of. At at. Possible. For. A. Few. Years etc; if there was an option, as well. As. Air. Conditioning on the lower level. A bit humid. But wonderful, beautiful home/condo, would. Go. Back any time. Currently looking for a home. On the area... It. Was. Beautiful. We are heading back on October. Hopefully that is an option while we look for a. New home. In the..."Reviewed August 3, 2026Roundtrip • Chicago (CHI) - Rutland (RUT)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,201$1,023found 1 day agoper traveler
Shoreham Hotel Deals
Best Western Plus Ticonderoga Inn & Suites
Best Western Plus Ticonderoga Inn & Suites
Frequently Asked Questions
How much does a Shoreham vacation package cost?
Offering great value package deals from $904 on Expedia, you'll be surprised at how little a vacation to Shoreham costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Shoreham?
If you're hoping to score a cheap Shoreham vacation package, consider visiting in January, September and December. You'll typically find lower rates on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Shoreham?
With a well-planned itinerary, you can easily hit the top Shoreham sights in a few days. But if you prefer to discover hidden spots or go on day trips, think about booking your Shoreham vacation for longer.
How to find the best Shoreham package deals?
Begin your search for a Shoreham package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Shoreham package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Shoreham adventure off to a flying start.
Is it cheaper to book a Shoreham vacation as a package?
You can enjoy significant savings on your Shoreham retreat by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Shoreham?
Score incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Shoreham getaway.
Does Expedia offer Book Now, Pay Later Shoreham vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Shoreham trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.