Cheap Hotels & Resorts in Winchester

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The Dagny Boston

The Dagny Boston

10/10 Excellent
"We Loved this place! Our favorite!"
Lisa 3-night trip
Posted 20 hours ago
The Dagny Boston

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is Winchester like for travellers on a budget?
Check out discount places to stay in Winchester on Expedia.com and book a trip that matches your budget. You can scroll through a wide offering of accommodation choices with Member Prices to find great deals and earn rewards. With our site's helpful page filters, you can search by price per night, or by amenities that customers often look for like free parking and free airport transport. If you're interested in affordable options near specific attractions, such as Middlesex Fells Reservation or Winter Pond, try filtering by location to refine your search. As you browse, click the heart button to keep track of your favourites so that you can return to them easily and make your final decision. Need a flight or a rental car along with your hotel? Choose from the Bundle and Save holiday packages and discover more amazing deals by arranging transport at the same time.
When is the best time for a budget trip to Winchester?
Weather will likely play an important role when you plan your trip to Winchester, but bear in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.
What is there to see and do in Winchester?
You don't need to spend big to find places to visit in Winchester. You can budget for the top local attractions that interest you most, such as TD Garden and Fenway Park, and then look for sights and activities that cost little or nothing at all. Check out the area's cultural spots like Somerville Theatre and Harvard Museum of Natural History, or get outdoors at Winter Pond.
How can I get to Winchester and get around on a budget?
Scoping out the transportation options in Winchester can help keep you on budget. The most convenient airport is 7.7 mi (12.3 km) from the centre in Bedford, MA (BED-Laurence G. Hanscom Field). However, if that doesn't suit your budget, you can look into flights to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away. To explore the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station.