Book Cheap Hotels in Winchester

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Most frequently booked Winchester hotels

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
14.02 km from city centre
The price is CA $333 per night
CA $333
CA $444 total
Oct 31 - Nov 1
includes taxes & fees
Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
11.44 km from city centre
The price is CA $319 per night
CA $319
CA $372 total
Oct 5 - Oct 6
includes taxes & fees
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Free cancellation
Reserve now, pay when you stay
13.92 km from city centre
The price is CA $353 per night
CA $353
CA $418 total
Oct 12 - Oct 13
includes taxes & fees
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
12.59 km from city centre
The price is CA $529 per night
CA $529
CA $665 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
13.02 km from city centre
Get rates
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Hilton Boston Logan Airport

Hilton Boston Logan Airport

4 out of 5
One Hotel Drive, Boston, MA
Free cancellation
Reserve now, pay when you stay
13.37 km from city centre
The price is CA $353 per night
CA $353
CA $411 total
Oct 31 - Nov 1
includes taxes & fees
Stay at this 4-star business-friendly hotel in Boston. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Harbor and New England Aquarium are located nearby.
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Free cancellation
Reserve now, pay when you stay
12.26 km from city centre
The price is CA $333 per night
CA $333
CA $388 total
Oct 5 - Oct 6
includes taxes & fees
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St, Boston, MA
Free cancellation
Reserve now, pay when you stay
12.64 km from city centre
The price is CA $732 per night
CA $732
CA $852 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway, Everett, MA
Free cancellation
Reserve now, pay when you stay
8.6 km from city centre
The price is CA $422 per night
CA $422
CA $471 total
Oct 30 - Oct 31
includes taxes & fees
Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Spa
Parking included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Winchester for Extended Stay

Crescent Suites Hotel

Crescent Suites Hotel

287 Crescent Street, Waltham, MA
9.4/10 Exceptional! (1,093 reviews)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winchester hotels essential information

Accommodation
3,791 hotels
Lowest Price
CA $338
Highest Price
CA $852
Popular hotels
Omni Boston Hotel at the Seaport, citizenM Boston North Station, Seaport Hotel Boston, The Dagny Boston, The Revolution Hotel, Hilton Boston Logan Airport, citizenM Boston Back Bay, The Langham, Boston, Encore Boston Harbor

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
From cool amenities to rooms with bunk beds, kid-friendly hotels are equipped with features that can help transform a nice family vacation into an amazing one. These Winchester properties make vacationing with your youngsters a piece of cake: Your crew will love staying at Private home near amazing downtown Woburn! Sleeps 9. A nearby theme park and a travel crib are just a few of the things that help make this property a popular option. Alternatively, spend your Winchester break at Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93. Make the most of a water park, a nearby theme park and more here.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is CA $338 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 3,791 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Great staff"
A verified traveller stayed at Sheraton Boston, a Marriott Hotel
Sheraton Boston, a Marriott Hotel

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