Winhall Vacations from $556

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Your Winhall Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Winhall vacation package. Check out hotels located in Bromley Mountain, which is great for views, families and nature. A trip to Winhall wouldn't be complete without visiting a few major attractions, starting with Stratton Mountain Golf Course. A few quick clicks is all it takes to craft the ultimate Winhall vacation on Expedia.

The Latest Winhall vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $747, price is now $556 per person
$556
per person
Feb 13 - Feb 15
found 8 hours ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The staff was very welcoming and attentive. Room was clean.

Reviewed on Jan 3, 2026

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $1,117, price is now $817 per person
$817
per person
Feb 10 - Feb 17
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
Staff was welcoming. When I did have a problem it was taken care of quickly.

Reviewed on Dec 24, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $2,025, price is now $1,524 per person
$1,524
per person
Feb 19 - Feb 22
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,169, price is now $955 per person
$955
per person
Feb 10 - Feb 17
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
We did not get breakfast; I do not believe it was included.

Reviewed on Jan 7, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $2,468, price is now $2,047 per person
$2,047
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Rutland (RUT)
No reviews
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Discover the most popular places to visit in Winhall

Stratton Mountain Golf Course

Play a round of golf at Stratton Mountain Golf Course and enjoy other activities in Winhall such as skiing. Discover the mountain views in this quaint area.

Stratton Mountain Golf Course

Winhall Hotel Deals

Bromley View Inn

Bromley View Inn

3.5 out of 5
522 VT Route 30 Bondville VT
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $131 total per night from Jan 14 to Jan 15
$131 total
Jan 14 - Jan 15
Total with taxes and fees
9/10 Wonderful! (406 reviews)
Really cute place with great amenities

Reviewed on Dec 15, 2025

Bromley View Inn
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica VT
$1,006 nightly
The price is $1,137 total per night from Jan 19 to Jan 20
$1,137 total
Jan 19 - Jan 20
Total with taxes and fees
9.6/10 Exceptional! (22 reviews)
I stayed here for a few days in October with friends. We had some initial confusion with the door locks, but the hosts were able to resolve it quickly.Great location, tons of sleeping and living space, and the hot tub was a welcome addition. We had a great time and would recommend this spot.

Reviewed on Nov 28, 2025

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$161 nightly
The price is $175 total per night from Jan 14 to Jan 15
$175 total
Jan 14 - Jan 15
Total with taxes and fees
8.8/10 Excellent! (942 reviews)
Nice hotel! Very friendly staff and great value compared to other accommodations.

Reviewed on Jan 4, 2026

Pointe at Castle Hill Resort
See all 2,736 properties in Winhall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Winhall Vacation Packages

Winhall Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)

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Frequently asked questions

How much does a Winhall vacation package cost?
You'll find cheap prices from $556 on Expedia for your Winhall escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winhall costs.
What are the cheapest months to go to Winhall?
You can usually find lower prices and greater availability in March, April and October. Browse our cheap Winhall vacation packages and you could land some great off-season discounts.
How many days is enough for Winhall?
Typically, a handful of days is enough to go to the major attractions during your Winhall vacation. However, if you want to have some time to relax or go on day trips, think about extending your trip.
How to find the best Winhall package deals?
Use Expedia's handy filters to find some great Winhall package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Winhall package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Winhall vacation as a package?
You can enjoy significant savings on your next Winhall escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winhall?
Score incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Winhall vacation.
How to plan a trip to Winhall?

  1. Choose when to go: Check your schedule and pack your bags. Your favorite season and the type of activities on offer will also help you decide when to escape to Winhall.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your accommodations will probably be the biggest expense during your trip to Winhall.
  3. Use our trip planning tool to discover Winhall: Research every aspect of your trip to Winhall with this handy planner. Invite your family and friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you're up to speed on Winhall, you can work out the right length of your vacation. Create a draft itinerary and give yourself enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Winhall vacation package.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some incredible things to do in Winhall. Book tickets or make reservations as soon as you can to save time and skip the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Winhall vacation packages?
Your Winhall getaway is meant to be a relaxing escape from your daily routine, not a source of money worries. So to allow you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.