Book Cheap Hotels in Winchester

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check hotel availability in Winchester

Tonight
Check prices in Winchester for tonight, Apr 2 - Apr 3
Apr 2 - Apr 3
Tomorrow night
Check prices in Winchester for tomorrow night, Apr 3 - Apr 4
Apr 3 - Apr 4
This weekend
Check prices in Winchester for this weekend, Apr 3 - Apr 5
Apr 3 - Apr 5
Next weekend
Check prices in Winchester for next weekend, Apr 10 - Apr 12
Apr 10 - Apr 12

Most frequently booked Winchester hotels

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 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 $214 per night
CA $214
CA $306 total
Apr 5 - Apr 6
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 Common are located nearby.
Pool
Hot tub
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 $176 per night
CA $176
CA $253 total
Apr 5 - Apr 6
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 Boston Common are located nearby.
Pool
Pet-friendly
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Free cancellation
Reserve now, pay when you stay
12.54 km from city centre
The price is CA $228 per night
CA $228
CA $323 total
Apr 5 - Apr 6
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.
Pet-friendly
Free WiFi
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
12.45 km from city centre
The price is CA $186 per night
CA $186
CA $217 total
Apr 5 - Apr 6
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.
Free WiFi
Restaurant
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
The price is CA $158 per night
CA $158
CA $184 total
Apr 5 - Apr 6
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.
Pet-friendly
Free WiFi
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 $249 per night
CA $249
CA $338 total
Apr 5 - Apr 6
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 Common are located nearby.
Omni Parker House

Omni Parker House

4.5 out of 5
60 School St Boston MA
Free cancellation
Reserve now, pay when you stay
12.26 km from city centre
The price is CA $341 per night
CA $341
CA $445 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Pet-friendly
Free WiFi
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 $236 per night
CA $236
CA $275 total
Apr 6 - Apr 7
includes taxes & fees
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square are located nearby.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St Boston MA
Free cancellation
Reserve now, pay when you stay
12.51 km from city centre
The price is CA $304 per night
CA $304
CA $354 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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
The price is CA $199 per night from Apr 3 to Apr 4
CA $199
CA $222 total
Apr 3 - Apr 4
includes taxes & fees
9.6/10 Exceptional! (1,163 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
4,094 hotels
Lowest Price
CA $184
Highest Price
CA $514
Popular hotels
Omni Boston Hotel at the Seaport, Seaport Hotel Boston, Hilton Boston Park Plaza, Harborside Inn Of Boston, The Revolution Hotel, The Dagny Boston, Omni Parker House , citizenM Boston Back Bay, Club Quarters Hotel Faneuil Hall, Boston

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 $184 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 4,094 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

The Dagny Boston

The Dagny Boston

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Great!!"
A verified traveller stayed at The Dagny Boston
The Dagny Boston