Name: Pointe at Castle Hill Resort
Price range: $160 total
Rating: 8.8

Your Windsor County Vacation

With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.

Top destinations in Windsor County

The Latest Windsor County Vacation Packages

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

Windham Hill Inn

$854

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Springfield (VSF)

8.6/10 Excellent! (37 reviews)

The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.

Reviewed on Jul 11, 2025

Deerfield Valley Inn

Save 100% on your flight

$1,396

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Springfield (VSF)

9.6/10 Exceptional! (84 reviews)

We had a nice room that was very comfortable. the owner was very friendly and accomodating.

Reviewed on Feb 20, 2026

Stone Hearth Inn and Eatery

$937

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Springfield (VSF)

9.2/10 Wonderful! (106 reviews)

So great all around!

Reviewed on Jan 4, 2026

Mount Snow Grand Summit Resort

$1,058

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Springfield (VSF)

8.8/10 Excellent! (242 reviews)

Staff was great, location terrific, restaurant/bar very nice, room was really nice, kitchen well equipped

Reviewed on Jan 19, 2026

Mount Snow Lodging

$913

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Springfield (VSF)

7.8/10 Good! (23 reviews)

The room hotel was very nice. The parking lot was very icy and snowy and the indoor hot tub had a lot of chlorine odor coming from it so we couldn't use that because we had a baby and it was too much smelling like chlorine. Great location though to go skiing

Reviewed on Apr 9, 2025

Find the Best Windsor County Vacation Packages

Windsor County Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Rutland Southern Vermont Regional Airport (RUT)
Top Sights	Buttermilk Falls, Echo Lake and Lake Rescue

Windsor County Hotel Deals

Align Inn Vermont

5817 Woodstock Rd Quechee VT

Fully refundableReserve now, pay when you stay

$120 nightly

$132 total

Feb 22 - Feb 23

Total with taxes and fees

9.4/10 Exceptional! (1,118 reviews)

This is one of our favorite hotels in Vermont, so clean and comfortable, Chelsea is beyond kind and accommodating!

Reviewed on Feb 20, 2026

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$148 nightly

$160 total

Mar 1 - Mar 2

Total with taxes and fees

8.8/10 Excellent! (984 reviews)

We stayed one night in room 107. It was roomier than many other hotels these days and had a comfortable bed. We were pleasantly surprised to have a mini fridge that actually worked. Furniture is a bit worn and the carpet has some mileage on it. Bathroom was clean and shower worked well. The hot tub ...

Reviewed on Feb 17, 2026

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$339 nightly

$373 total

Feb 22 - Feb 23

Total with taxes and fees

9.2/10 Wonderful! (565 reviews)

Very clean, high end, friendly staff

Reviewed on Feb 20, 2026

See all 1,361 properties in Windsor County

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.