Book Cheap Hotels in Winchester

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Most frequently booked Winchester hotels

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA

11.24 km from city centre

CA $202

CA $277 total

Jul 26 - Jul 27

includes taxes & fees

Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.

Seaport Hotel Boston

1 Seaport Lane Boston MA

Free cancellation

Reserve now, pay when you stay

13.92 km from city centre

CA $268

CA $361 total

Jul 26 - Jul 27

includes taxes & fees

Book a stay at this business-friendly 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 Revolution Hotel

40 Berkeley Street Boston MA

Free cancellation

Reserve now, pay when you stay

13.02 km from city centre

CA $226

CA $263 total

Aug 2 - Aug 3

includes taxes & fees

Stay at this 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.

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free cancellation

Reserve now, pay when you stay

14.02 km from city centre

CA $328

CA $440 total

Jul 7 - Jul 8

includes taxes & fees

Book a stay at this luxury 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 Boston Harbor are located nearby.

Pool

Hot tub

Harborside Inn Of Boston

185 State St Boston MA

12.45 km from city centre

CA $318

CA $371 total

Jul 26 - Jul 27

includes taxes & fees

Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.

The Langham, Boston

250 Franklin St Boston MA

Free cancellation

Reserve now, pay when you stay

12.62 km from city centre

CA $646

CA $752 total

Aug 2 - Aug 3

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.

The Dagny Boston

89 Broad Street Boston MA

Free cancellation

Reserve now, pay when you stay

12.59 km from city centre

CA $317

CA $419 total

Jul 26 - Jul 27

includes taxes & fees

Book a stay at this 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 New England Aquarium and Boston Harbor are located nearby.

The Midtown Hotel MOD Collection by Sonesta

220 Huntington Avenue Boston MA

Free cancellation

Reserve now, pay when you stay

12.85 km from city centre

CA $230

CA $268 total

Jul 26 - Jul 27

includes taxes & fees

Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.

Hilton Boston Park Plaza

50 Park Plaza Boston MA

Free cancellation

Reserve now, pay when you stay

12.54 km from city centre

CA $244

CA $342 total

Jul 26 - Jul 27

includes taxes & fees

Book a stay at this luxury hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

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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

287 Crescent Street Waltham MA

CA $218

CA $244 total

Aug 1 - Aug 2

includes taxes & fees

9.6/10 Exceptional! (1,225 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	4,172 hotels
Lowest Price	CA $234
Highest Price	CA $752
Popular hotels	Hyatt Regency Boston/Cambridge, Seaport Hotel Boston, The Revolution Hotel, Omni Boston Hotel at the Seaport, Harborside Inn Of Boston, The Langham, Boston, The Dagny Boston, The Midtown Hotel MOD Collection by Sonesta, Hilton Boston Park Plaza

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 $234 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 4,172 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.