Name: Pointe at Castle Hill Resort
Price range: $156 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.

The Mountain Inn at Killington

$697

per person

May 8 - May 11

found 19 hours ago

Roundtrip flight included

Wilmington (ILG) to Rutland (RUT)

9.2/10 Wonderful! (1,005 reviews)

Nice place close to the mountain with an attentive and friendly staff. Very clean and well run. It’s not a resort or a place where you stay to enjoy the hotel. You are here to ski / board and this is your place to return to for drinks and a good night sleep. The AC wasn’t working well when we were there but it was still late Winter so not unexpected (was unseasonably warm). The furniture in the sitting areas upstairs needs to be upgraded since that’s really the only place to hangout in morning or afternoons other than the restaurant. Overall very pleased with the place for the price.

Reviewed on Apr 2, 2026

Comfort Inn Rutland - Killington

$714

per person

May 8 - May 11

found 19 hours ago

Roundtrip flight included

Wilmington (ILG) to Rutland (RUT)

8/10 Very Good! (1,010 reviews)

Clean room, convenient location

Reviewed on Apr 6, 2026

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

Save 100% on your flight

$5,715

per person

May 8 - May 11

found 19 hours ago

Roundtrip flight included

Wilmington (ILG) to Rutland (RUT)

No reviews

North Star Lodge and Resort

$705

per person

May 8 - May 11

found 19 hours ago

Roundtrip flight included

Wilmington (ILG) to Rutland (RUT)

8.6/10 Excellent! (1,003 reviews)

Bar is a great touch!

Reviewed on Apr 1, 2026

Mountain Green Resort

$894

per person

May 8 - May 11

found 19 hours ago

Roundtrip flight included

Wilmington (ILG) to Rutland (RUT)

4/10 (2 reviews)

Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 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

$119 nightly

$131 total

Apr 8 - Apr 9

Total with taxes and fees

9.4/10 Exceptional! (1,152 reviews)

Clean room, friendly staff, good breakfast. Always enjoy staying at the Inn. 👍👍

Reviewed on Apr 5, 2026

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$144 nightly

$156 total

Apr 12 - Apr 13

Total with taxes and fees

8.8/10 Excellent! (1,003 reviews)

Have stayed here many times. Close to town and Okemo. Very convenient.

Reviewed on Mar 30, 2026

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$349 nightly

$384 total

Apr 20 - Apr 21

Total with taxes and fees

9.4/10 Exceptional! (571 reviews)

Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍

Reviewed on Apr 5, 2026

See all 1,382 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.