Find 3,228 hotels in Winchester

Finding Winchester Hotels

Winchester is a good place to visit, but if it's hard to find accommodation and you find yourself searching for more options, these towns that are nearby might have more of what you like.

• 41 hotels in Woburn
• 6 hotels in Stoneham
• 23 hotels in Arlington

Top Hotels and Other Accommodation Options in Winchester

When you're deciding where you want to stay in Winchester, you can easily and quickly search ebookers for hotels offering services such as high-speed Internet, free airport transport or a swimming pool. You can use the filters to narrow down your search for a hotel, so you get the services that are important to you, such as air conditioning or an in-room kitchen.

This Winchester hotel is liked by guests for the pool:

• Private Room in Shared Apartment, Free Wifi and Parking, no Hidden Fees

Exploring Winchester

The city of Winchester has some interesting things to see and do. Popular attractions in and around Winchester include:

• Winter Pond
• Middlesex Fells Reservation
• Fenway Park
• Encore Boston Harbor
• Harvard Square
• TD Garden
• Boston Common

When making plans for your trip to Winchester, you can also use ebookers to look for a convenient flight into Bedford, MA (BED-Laurence G. Hanscom Field) Airport. You can narrow down your search by number of stops, airline or time of departure to find the one that works best for you.

When is the Best Time to Explore Winchester?

If you're wondering when is the best time of year to explore Winchester, you might find this info about seasonal weather helpful when planning your trip. The warmest months in Winchester are typically July and August, whereas the coldest months are usually January and February. The months with the most rain are December and October, whereas May and September have the least.

Here's an overview on how much rain you can expect and what the temperatures are going to be like:

• From January to March, the average daytime temperature is 7°C and at night it is -5°C. Seasonal average rainfall is 305 mm.
• If you visit between April and June, you can expect an average temp of 24°C during the day and 5°C at night. Average rainfall during this season is 286 mm.
• The daytime average temp from July to September is 28°C and the night-time average is 15°C. Average precipitation for this season is 307 mm.
• Between October and December, the average temp during the day is 17°C and -1°C at night. Seasonal average rain is 337 mm.
• Average annual rainfall in Winchester is 1236 mm.