Windham County Holidays

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Your Windham County Holiday

When adventure calls, answer it with a tailor-made holiday package to Windham County. Wherever it is you're going and whatever you have planned, get ready to immerse yourself in a destination with plenty to offer. Your trip to Windham County wouldn't be complete without experiencing some of its most renowned cities, starting with Stratton. Two of the most popular attractions here include Stratton Mountain Resort and Mount Snow. Wilmington should also be on the itineraries of all Windham County travellers. Visitors to this destination enjoy Mount Snow and Mount Snow Golf Course. Expedia has flights, hotels, car rentals and more to help you put together your very own tailored Windham County holiday today.

Top destinations in Windham County

A canoe on calm water with a forested hill in the background.
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West Dover

West Dover
A forest with autumn foliage reflecting in a calm lake.
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Stratton

Stratton

Top Windham County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was £1,026, price is now £982 per person
£982
per person
26 Dec - 29 Dec
found 1 day ago
Return direct flight included
London (LHR) to Rutland (RUT)
9.4/10 Exceptional! (608 reviews)

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was £1,298, price is now £1,137 per person
£1,137
per person
26 Dec - 29 Dec
found 1 day ago
Return direct flight included
London (LHR) to Rutland (RUT)
9/10 Wonderful! (890 reviews)

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was £1,249, price is now £1,096 per person
£1,096
per person
26 Dec - 29 Dec
found 1 day ago
Return direct flight included
London (LHR) to Springfield (VSF)
10/10 Exceptional! (250 reviews)

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was £1,066, price is now £1,007 per person
£1,007
per person
26 Dec - 29 Dec
found 1 day ago
Return direct flight included
London (LHR) to Springfield (VSF)
8.6/10 Excellent! (1,011 reviews)

The Hermitage Inn Vermont

The Hermitage Inn Vermont

4 out of 5
Price was £1,640, price is now £1,566 per person
£1,566
per person
26 Dec - 29 Dec
found 1 day ago
Return direct flight included
London (LHR) to Springfield (VSF)
9/10 Wonderful! (19 reviews)
Could not have had a more perfect stay. Highly recommend.

Reviewed on 2 Nov 2026

Windham County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Albany Intl. Airport (ALB)
Top Sights
Molly Stark State Park, Lowell Lake State Park and The Ledge

Top hotels in Windham County

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundable
The price is £141 per night from 9 Nov to 10 Nov
£141
9 Nov - 10 Nov
includes taxes & fees
Grand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is £70 per night from 10 Nov to 11 Nov
£70
10 Nov - 11 Nov
includes taxes & fees
Colonial Motel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is £89 per night from 10 Nov to 11 Nov
£89
10 Nov - 11 Nov
includes taxes & fees
Latchis Hotel
See all 1,369 properties in Windham 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 Windham County travel package cost?
Starting from just £982, a travel package is your ticket to low-priced travel. Custom make your Windham County adventure by picking from our huge range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Windham County travel package?
If your travel plans in Windham County have been upended, it's good to know that it's possible to amend or cancel your booking. If you booked within the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Windham County?
Bundling your flight and hotel with Expedia won't just save you time — it'll save you a pretty penny too. A Windham County travel package makes it a cinch to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule won't be a problem. In addition to that, we've got over 1,000,000 properties globally to choose from. Now that's what we call choice. Whatever your budget, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Windham County holidays?
Expedia has partnered with online lender Klarna to make your next break easier on the purse strings. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: If you'd like to pay for your getaway in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you want to grab an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.

What are the top hotels in Windham County?
Take a look at Colonial Motel And Spa and Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel. They're top picks for lots of travellers to Wilmington. If Stratton features in your travel plans, Colonial Motel And Spa and Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel are two top-notch options.
How far in advance should I book my Windham County holiday?
Reserving your flight early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. Usually, this is the cheapest time to book. If circumstances have left you booking late, discount flights to Windham County sometimes occur in the weeks leading up to departure.
What does an Expedia Windham County travel package include?
You can choose from a combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like activities and tours. Want to pick your airfare class? That's easily done too. The choice is yours when it comes to arranging your perfect Windham County trip.
What should I know before booking a Windham County travel package?
Our prices are always low. However, you'll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Windham County Expedia travel package?
Yes, and with over 550 airlines to select from around the world, you have loads of choice. Scroll through the available options and find out which airline fits your needs and budget.

Stay near popular Windham County attractions

A snow-covered forest with a clear sky.

Stratton Mountain Resort

9.2/10 (365 reviews)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
See properties

What to do in Windham County

Vermont RT 100 App-Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

£13
per traveller
80% of travellers recommend
Vermont RT 100 App-Guided Driving Audio Tour
Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

£71
per adult
Mindful Forest Escape: Rebalance, reflect and connect
Colonial Flintlock Musket Experience

Colonial Flintlock Musket Experience

£96
per adult
100% of travellers recommend
Colonial Flintlock Musket Experience
See all activities in Windham County

* 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.