A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Cheap Hotels & Resorts in Winchester from AU$146

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Check availability on Winchester Cheap Hotels

Tonight
18 Sept - 19 Sept
Tomorrow
19 Sept - 20 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Winchester cheap hotels

1. Hilton Boston/Woburn

Hilton Boston/Woburn
Woburn
United States
Shawna
AU$256
includes taxes & fees
27 Sept - 28 Sept
Hilton Boston/Woburn

2. Lakeside Inn

Lakeside Inn
Wakefield
United States
Marc
AU$146
includes taxes & fees
27 Sept - 28 Sept
Lakeside Inn

3. Holiday Inn Express Boston North-Woburn by IHG

Holiday Inn Express Boston North-Woburn by IHG
Woburn
United States
Greg
AU$202
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Boston North-Woburn by IHG

4. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
United States
Pamela
AU$272
includes taxes & fees
20 Sept - 21 Sept
Hampton Inn Boston Woburn

5. Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
Burlington
United States
Manuel
AU$209
includes taxes & fees
19 Oct - 20 Oct
Sonesta Simply Suites Boston Burlington

6. Residence Inn by Marriott Boston Burlington

Residence Inn by Marriott Boston Burlington
Burlington
United States
Sarah
AU$336
includes taxes & fees
19 Sept - 20 Sept
Residence Inn by Marriott Boston Burlington

7. Staybridge Suites Boston - Burlington by IHG

Staybridge Suites Boston - Burlington by IHG
Burlington
United States
hawa
AU$273
includes taxes & fees
20 Sept - 21 Sept
Staybridge Suites Boston - Burlington by IHG

8. Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
Burlington
United States
Joanne
AU$285
includes taxes & fees
27 Sept - 28 Sept
Archer Hotel Boston/Burlington

9. Porter Square Hotel

Porter Square Hotel
Porter Square
United States
Gerardo
AU$243
includes taxes & fees
20 Sept - 21 Sept
Porter Square Hotel

10. Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
Waltham
United States
iram
AU$190
includes taxes & fees
20 Sept - 21 Sept
Hilton Garden Inn Boston/Waltham
View all properties

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Didn't get the room I reserved, so I went downstairs, talked to a different receptionist and she upgraded us to a better room than I originally booked. Great customer service."
Kelly 1-night trip
Posted 1 hour ago
Harborside Inn Of Boston
Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Excellent!"
Kim 2-night trip
Posted 2 hours ago
Seaport Hotel Boston
The Dagny Boston

The Dagny Boston

10/10 Excellent
"We had a wonderful stay. The rooms are spacious, very clean, and well suited for a family with young kids. You can’t be its location. We walked everywhere with the exception of using the subway for a Red Sox game, which was also super easy to navigate! We will definitely stay again the next time we come to Boston."
Kelly 3-night trip
Posted 3 hours ago
The Dagny Boston
Omni Parker House

Omni Parker House

8/10 Good
"Great central location to tourist sites. Beautiful hotel lobby and common spaces. Very nice staff at front desk and restaurants."
Elly 3-night trip
Posted 4 hours ago
Omni Parker House
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"Nice place to stay. Loved the outdoor fire pit at night. A little far from downtown area and urbers added up but had a great stay"
Stacey 2-night trip
Posted 5 hours ago
Hyatt Regency Boston Harbor
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Clean rooms, friendly staff, & great service"
Gabrielle 2-night trip
Posted 1 day ago
Hilton Boston Park Plaza
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

8/10 Good
"Very helpful staff. Clean room. No breakfast. Very expensive parking, Very good location walking distance to most places."
jim 3-night trip
Posted 1 day ago
The Westin Copley Place, Boston, a Marriott Hotel

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 Winter Pond or Middlesex Fells Reservation, 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 Fenway Park and Encore Boston Harbor, 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.

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