Destination guide

Travel to scenic Windsor

The forests, mountains and countryside display a scene truly unique to Windsor. Travellers to this scenic city praise the golfing, hiking and bird watching. Okemo Mountain Resort and Killington Resort are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.


Sightseeing in and around Windsor

Are you searching for attractions to visit while you're in the area? Venture out of your holiday home and experience everything that makes Windsor a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Okemo Mountain Resort (15 mi / 24.2 km)
  • Killington Resort (19.5 mi / 31.4 km)
  • Union Arena Community Center (9.2 mi / 14.8 km)
  • Quechee State Park (9.8 mi / 15.7 km)
  • Vermont Institiute of Natural Science (10 mi / 16.2 km)
  • Quechee Ski Hill (10.9 mi / 17.5 km)
Natural features

Exploring the natural landscape of Windsor

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Windsor is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Path of Life Garden (2.6 mi / 4.2 km)
  • Mt Ascutney State Park (3.7 mi / 6 km)
  • Billings Park and Trail (9.3 mi / 14.9 km)
  • Quechee Gorge (9.8 mi / 15.7 km)
  • Quechee State Park (9.8 mi / 15.7 km)
  • Mount Tom Peak (9.9 mi / 15.9 km)
How to get there

How to get to and around Windsor

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 11.2 mi (18 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Springfield, VT (VSF-Hartness State), which is 11.4 mi (18.3 km) away.

If you'd prefer to travel by train, the main station serving the city is Windsor Station.

How many holiday rentals are available around Windsor?

Our 2020 accommodation listings offer a large selection of 314 holiday lettings around Windsor. From 186 houses to 60 flats & apartments, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent a mountain-view property in Windsor?

What an incredible view! That's what you'll be exclaiming when you head for the hills and enjoy a tranquil high-altitude escape. HomeAway has no less than 117 alpine getaway rentals available. Of course, that may not be quite your holiday style. Fortunately, HomeAway has loads more options, including:

  • 82 rural holiday accommodation options.
  • 81 mountainside holiday accommodation options.
  • 77 village holiday accommodation options.

Can I rent a house in Windsor?

Our house holiday rentals are real accommodation for real travellers. Offering plenty of space to spread out, they're perfect for those who want to experience life like a local. There are 183 options currently listed on HomeAway. Prices start at £92 a night. Or perhaps you'd rather choose one of the area's other self-catering accommodation options, like:

  • Condo: 50 self-catering accommodation options. Prices start from £35 per night.
  • Townhome: 19 self-catering accommodation options. Prices start from £130 per night.
  • Cabin: 12 self-catering accommodation options. Prices start from £73 per night.

Can I stay in Windsor in a large group?

It can be difficult finding the time to relax with close friends and family. A group getaway is the perfect opportunity to get together. If you were hoping to stay under the same roof, HomeAway has places for you. House holiday rentals are the most popular option here for large groups of guests. Our worldwide database presently has 50 available. If you're hoping to travel in a big group, the property options that will suit your needs include:

  • If yours is a crew of 8, we have 138 rental accommodation appropriate for that size. Spend a night for as little as £80.
  • Looking for a rental property for 6 people? We have 107 that will serve you well. You can get one for as low as £35 a night.
  • Travelling with 10 guests? We offer 102 rental accommodation that will be ideal. Prices start from £90 per night.

You and all your mates will be more than satisfied when you book your Windsor escape through us!

Where are the cheapest holiday rentals in Windsor?

HomeAway has plenty of fantastic budget-concious possibilities. Treat your posse to a fancy meal out or extend your holiday for a few nights with all the cash you'll have leftover. West Woodstock is a fantastic area to investigate if you want to keep your budget under control. HomeAway has 19 holiday rentals, and the average price is a very affordable £243 per night. Quechee is another place to check out. We have holiday rentals here, and the average price is around £251 a night.