Discover a selection of 390 vacation rentals in Windham, VT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $150 per night, and houses and condos are popular options for a stay in Windham. Either way, you'll find a rental for everyone's needs.
Destination guide

Choose a vacation rental for your Windham getaway

Experience the unique character of Windham with a stay in a vacation home rental. This city has something for everyone. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Activities and attractions in Windham

Are you searching for top things to see and do during your stay? Venture out of your cozy vacation rental and check out everything that makes Windham a fun place to get away. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Okemo Mountain Resort (14 mi / 22.6 km)
  • Magic Mountain Ski Resort (2.6 mi / 4.1 km)
  • Viking Nordic Center (3.7 mi / 5.9 km)
  • Jamaica State Park (6 mi / 9.7 km)
  • Stratton Mountain Golf Course (10.5 mi / 16.8 km)
  • Bromley Mountain Ski Resort (10.7 mi / 17.2 km)
Natural features

Exploring the natural features in Windham

Whether you're an outdoor enthusiast or just want to take in the scenery, Windham is a great spot to appreciate mother nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Lowell Lake State Park (2.8 mi / 4.5 km)
  • Ball Mountain State Park (5.6 mi / 9 km)
  • Grafton Ponds Outdoor Center (5.9 mi / 9.5 km)
  • Jamaica State Park (6 mi / 9.7 km)
  • Dorsey Park (13.6 mi / 21.8 km)
  • Emerald Lake State Park (15.3 mi / 24.7 km)
How to get there

Transportation to and around Windham

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 14.2 mi (22.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away.

How many vacation rentals are available around Windham, VT?

Our 2020 property listings offer a large selection of 390 vacation rentals around Windham. From 207 house rentals to 91 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Windham?

We all adore a room with a view. But if you're craving views that'll make you feel like you're on cloud nine, you'll have to head for the hills. Vrbo has 165 alpine rentals available. After a different setting? See if any of our other properties take your fancy. Our range here includes:

  • 81 mountainside vacation rentals.
  • 70 rural vacation rentals.
  • 65 village vacation rentals.

Can I rent a house in Windham?

If you're seeking a home away from home for your upcoming vacation, renting a whole house is a terrific idea. You and your group will have the space you need for all sorts of vacation activities. There are 201 houses currently listed on Vrbo. Prices start at $80 per night. Or perhaps you'd rather go for one of the area's other sought-after lodging options, like:

  • Condo: 84 vacation homes. Prices start from $102 per night.
  • Townhome: 27 vacation homes. Prices start from $132 per night.
  • Farmhouse: 16 vacation homes. Prices start from $133 per night.

Can I stay in Windham in a large group?

It can be hard finding the time to relax with friends and family. A group trip is the perfect opportunity to reunite and unwind. If you were planning to kick back together, Vrbo has options to suit. House vacation homes are the preferred choice for large groups of visitors, with 39 available here. In the area, the rental properties that are suitable for bigger groups include:

  • If yours is a group of 8, we have 84 vacation homes suited to that size. Spend a night for as little as $80.
  • If you've got 6 in your crew, you'll be delighted to learn that there are 81 vacation homes suitable. Prices begin at just $90 per night.
  • Trying to find rentals to suit 10 people? You'll be delighted to hear we have 78 that will fit the bill. You can grab one for as little as $130 per night.

You and all your besties will be more than satisfied when you organize your Windham vacation with us!

Where are the cheapest rentals in Windham?

Friends become our chosen family. Write a new chapter with those you hold dearest and book an affordable stay with Vrbo. Okemo Mountain Resort is a bargain-hunter's dream. And with 190 Vrbo rentals at an average price of $335 a night, it's not difficult to see why. Another 10 Vrbo rentals are on offer in or around Mountain Acres. With an average price of $422 a night, you're sure to snatch a deal worth bragging about.

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