Windsor County Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Your Windsor County Holiday

With a Windsor County holiday 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 holiday to the second you come back home, Expedia will take care of you each step of the way.

Top destinations in Windsor County

Woodstock featuring a house
FlightsFlightsHotelsHotels

Woodstock

Woodstock

Top Windsor County Flight + Hotel Deals

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

Mountaineer Inn

2 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (495 reviews)
I love staying at the Mountaineer. I stay there every time I go to Vermont. The staff is very friendly and welcoming. Parking is very easy good location, central to many restaurants and other amenities. Very nice coffee bar beautiful pool for swimming. great atmosphere. Love the easy check-inprocess. Everything is digital no keys to worry about.

Reviewed on 6 Aug 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Save 100% on your flight
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Springfield (VSF)
9.6/10 Exceptional! (54 reviews)
everybody was so kind! we had a wonderful room for such a cheap price, I couldn't resist to choose this inn. The house keeper was so sweet and so was the owner! I will definitely be coming back :)

Reviewed on 29 Jul 2025

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Rutland (RUT)
9/10 Wonderful! (39 reviews)
The customer service was excellent!

Reviewed on 14 Jul 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
Great little place. Very friendly and clean.

Reviewed on 31 Jul 2025

The Vermont Inn

The Vermont Inn

3 out of 5
per person
1 Oct - 8 Oct
found 1 day ago
Return direct flight included
London (LON) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on 23 Jul 2025

Windsor County Essential Information

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

Top hotels in Windsor County

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is £367 per night from 1 Sept to 2 Sept
£367
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (530 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 Jul 2025

Woodstock Inn & Resort
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is £104 per night from 18 Aug to 19 Aug
£104
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
Good room.
"Nice clean room, sight get a chance to enjoy the pool or pond."

Reviewed on 4 Aug 2025

Align Inn Vermont
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is £121 per night from 24 Aug to 25 Aug
£121
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (794 reviews)
"Beautiful pet friendly place in the heart of Woodstock Village. Scenery is lovely, soothing and plenty to do. Can walk to things, bike or hike."

Reviewed on 1 Aug 2025

The Shire Woodstock
See all 1,327 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Windsor County travel package cost?
The most affordable Windsor County travel package is £795, so your dream trip can become a reality — without spending a fortune. Bundle flights, hotels, car rentals and more to custom build a package suited to your travel style.
If I'm not able to travel, can I cancel my Windsor County travel package?
Yes, you can. We totally understand that things don't always go to plan, so we're here to help if you need to make changes to your Windsor County travel package. You may be able to amend or cancel your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Windsor County?
Bundle your hotels and flights, toss in extras such as tours, and save with a Windsor County holiday package. You won't just score big discounts on your trip — you'll have loads of choice too. When you book through Expedia, you can select from more than 550 airlines and 1,000,000 properties all over the world. Your next big adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later Windsor County holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a fantastic getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable monthly instalment plans. If paying small amounts each month works for you, choose this option at checkout.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Windsor County?
Ludlow is among the first stops on many travellers' Windsor County must-see lists. Okemo Mountain Resort might have something to do with it.
What are the top hotels in Windsor County?
White River Inn and Suites and Hotel Coolidge know how to make their guests feel at home in Ludlow. If you also plan to stay in Plymouth, check out White River Inn and Suites and Hotel Coolidge. Both are top picks with travellers.
How far in advance should I book my Windsor County holiday?
It all depends on the air carrier, but you can usually look up international flights on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travellers will sometimes nab a cheaper seat just weeks prior to departure dates.
What does an Expedia Windsor County travel package include?
Expedia has all you need to arrange your Windsor County escape, but what your package looks like depends on you. Select from any combination of rental cars, hotels and flights. After a few activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your budget, there's a package deal to meet your needs.
What should I know before booking a Windsor County travel package?
A travel package can be customized for your budget and is a simple way to make your budget go further. What you include is totally up to you. Hotels, rental cars and flights — choose any combination that works with your plans.
Can I choose my airline with a Windsor County Expedia travel package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Just pick the carrier that suits you and craft the perfect Windsor County trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.