Name: Hotel Coolidge
Price range: $117 total
Rating: 8.2

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.

Bentley House Bed and Breakfast

$589

per person

Jul 9 - Jul 13

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Rutland (RUT)

No reviews

The Shire Woodstock

$923

per person

Jul 9 - Jul 13

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

8.8/10 Excellent! (926 reviews)

Lovely hotel with views of river and walkable to variety of shops and restaurants

Reviewed on May 12, 2026

Latchis Hotel

$637

per person

Jul 9 - Jul 13

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

8.6/10 Excellent! (879 reviews)

Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!

Reviewed on May 15, 2026

My Place Hotel-Randolph VT

$658

per person

Jul 9 - Jul 13

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Lebanon (LEB)

9.4/10 Exceptional! (443 reviews)

Room was very clean & comfortable. Make sure to bring your own pots, pans, utensils, plates & so on as they are not provided with the room. If you don't have them with you, they sell sets at the front desk. Hotel was very quiet, never heard a TV or any noise from other guests.

Reviewed on May 21, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

$695

per person

Jul 9 - Jul 13

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

8.6/10 Excellent! (853 reviews)

I’ve stayed here with my two daughters multiple times and it’s always incredible.

Reviewed on May 17, 2026

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

$116 nightly

$128 total

May 24 - May 25

Total with taxes and fees

9.4/10 Exceptional! (1,193 reviews)

"Convenient location, easy check in experience, clean room , helpful staff and free breakfast. We would definitely stay there again."

Reviewed on May 22, 2026

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$359 nightly

$395 total

May 25 - May 26

Total with taxes and fees

9.4/10 Exceptional! (580 reviews)

"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Hotel Coolidge

39 South Main Street White River Junction VT

Fully refundableReserve now, pay when you stay

$106 nightly

$117 total

May 26 - May 27

Total with taxes and fees

8.2/10 Very Good! (1,000 reviews)

"I want my money back. The pictures are misleading on the website. It is a dark, smelly, falling apart hotel. DO NOT schedule a stay there ever. You have been warned. It needs to be condemned."

Reviewed on May 18, 2026

See all 1,357 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.