Book Hotels in Winchester, MA

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

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

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight
Jul 9 - Jul 10
Tomorrow
Jul 10 - Jul 11
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Winchester hotels

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street, Boston, MA
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $250 total per night from Jul 27 to Jul 28
$250 total
Jul 27 - Jul 28
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.
"The only dining options within walking distance we found were "fast food" options."

Reviewed on Jul 8, 2025

The Godfrey Hotel Boston
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Jul 13 to Jul 14
$214 total
Jul 13 - Jul 14
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a communal living room, and express check-in ...
"Check in was self serving and simple. Big fan of the room controls through the app and iPad in the room. Blackout curtains and complementary refillable water bottles are a fantastic incentive."

Reviewed on Jul 8, 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $203 total per night from Jul 20 to Jul 21
$203 total
Jul 20 - Jul 21
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
"Amazing location."

Reviewed on Jul 7, 2025

citizenM Boston North Station
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
$246 nightly
The price is $287 total per night from Aug 10 to Aug 11
$287 total
Aug 10 - Aug 11
Total includes taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks ...
"We just had a wonderful stay at the Omni seaport ! It was July 4th weekend so it was. Busy but still the hotel was very attentive and organized . From valet to front desk , to the pool staff everyone was friendly and helpful and also had in room dining for breakfast from kestra ans it was amazing ..."

Reviewed on Jul 8, 2025

Omni Boston Hotel at the Seaport
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
$229 nightly
The price is $267 total per night from Jul 13 to Jul 14
$267 total
Jul 13 - Jul 14
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on ...
"The beds were a little uncomfortable but other than that perfect"

Reviewed on Jul 8, 2025

Harborside Inn Of Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $190 total per night from Jul 27 to Jul 28
$190 total
Jul 27 - Jul 28
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, ...
Great location!
"Great people! Great location! Super clean!"

Reviewed on Jul 7, 2025

Hyatt Regency Boston/Cambridge
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $242 total per night from Jul 13 to Jul 14
$242 total
Jul 13 - Jul 14
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are ...
"Good place with the price."

Reviewed on Jul 8, 2025

The Revolution Hotel
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $176 total per night from Aug 10 to Aug 11
$176 total
Aug 10 - Aug 11
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, express check-out, and luggage storage are also ...
"Small but very clean room. The bed was incredibly comfortable. Friendly staff at the front desk."

Reviewed on Jul 9, 2025

Copley Square Hotel, a FOUND Hotel
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St, Brookline, MA
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $218 total per night from Jul 13 to Jul 14
$218 total
Jul 13 - Jul 14
Total includes taxes and fees
A 24-hour gym is featured at this hotel, along with self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage ...
"Would stay there again"

Reviewed on Jul 8, 2025

The Arcadian Hotel
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.

Winchester Hotel & Travel Guide

Apartment and hotel choices are in abundance in Winchester. If you want to be within a 6-mile (10-kilometer) radius of Winchester, our comprehensive database contains at least 68 hotel options that match that criteria.

Read about many hotels you can stay at within a 3 miles (5 kilometers) drive from Winchester's downtown, including the Hyatt Place Boston/Medford and Hilton Boston/Woburn.

Have a look at the Mandarin Oriental Boston or the Four Seasons Hotel Boston. The Mandarin Oriental Boston is only 8 miles (13 kilometers) from the town center of Winchester. The Four Seasons Hotel Boston, is located just 8 miles (13 kilometers) away. The The Ritz-Carlton, Boston and also the Fifteen Beacon are alternative accommodation options worth looking into in Winchester.

The extended Eastern Massachusetts district is well worth seeing for yourself too. Explore Eastern Massachusetts's churches and art museums. Outdoorsy types should leave time to check out the region's coastal plains. Visitors in this pocket of United States of America adore snowboarding and skiing.

Cambridge is 5 miles (9 kilometers) south of Winchester and features Harvard Square and Harvard University. A few Travelocity-listed Cambridge hotels include the Fairmont Copley Plaza, Boston and The Charles Hotel. For another option, head to Natick, 16 miles (25 kilometers) to the southwest of Winchester, where you can choose from the Crowne Plaza Boston-Natick and Courtyard by Marriott Boston Natick. The Natick Collection and Cochituate State Park are some of the most popular sites to get to know in Natick.

During your vacation, spend a few hours enjoying the spectacle with some of Boston's spectators at a community game. Fenway Park is 8 miles (12 kilometers) to the south of Winchester. Anybody hoping to find a room or apartment near to the sporting action can compare between the Marriott Vacation Club Pulse at Custom House, Boston or the The Colonnade Hotel Back Bay.

Logan International Airport is 9 miles (14 kilometers) away from Winchester's urban core. Enlightened travelers who choose to find a room nearby can look into a convenient option in the InterContinental Boston or Kimpton Nine Zero Hotel.

Top reasons for your vacation to Winchester

  • Proximity to soccer fields: Winchester is known for its close proximity to soccer fields, making it a great destination for families who enjoy the sport.
  • Family-friendly attractions: The town offers plenty of family-friendly attractions, including wildlife and birdwatching spots, where you can enjoy nature together.
  • Convenient for working parents: Winchester's proximity to business districts makes it convenient for working parents who still want to enjoy a family vacation.
  • Nature trails and birdwatching: Explore the beautiful nature trails and go birdwatching at the nearby lake, perfect for outdoor enthusiasts.
  • Quaint streets and charming shops: Take a leisurely stroll through Winchester's quaint streets and discover its rich history and charming shops.

Find your favorite hotels in Winchester

If you're planning a family vacation to Winchester, Massachusetts, you'll find a variety of hotel options to suit your needs. Whether you're looking for a budget-friendly option or a more luxurious stay, there are hotels in and near Winchester that offer comfortable accommodations. Many of these hotels are also family-friendly, providing amenities and services that cater to the needs of families traveling with children. With the closest hotels conveniently located, you'll have easy access to the attractions and sights in Winchester and the surrounding area.

Hotel nameTypeStarsDescription
Omni Parker HouseThis 4.0-star rated hotel is conveniently located 7.6 miles away from Winchester. It offers close proximity to historical sites, friendly people, monuments, the university, walking trails, theaters, ecotourism opportunities, sustainable practices, and kayaking. It is also near the airport, making it a convenient choice for travelers.
Omni Boston Hotel at the SeaportHotel4.5With a 4.5-star rating, this hotel is located 8.7 miles away from Winchester. It boasts luxurious accommodations and is known for its excellent service. Its proximity to the vibrant Seaport district makes it a great option for exploring the city.
The Revolution HotelHotel3.5This 3.5-star rated hotel is situated 8.1 miles away from Winchester. It offers a unique experience with its urban setting, skyscrapers, architectural beauty, walking opportunities, entertainment venues, cathedral, friendly locals, scenic views, and charming cafes and churches.

Explore the best activities and sights in Winchester

Winchester, Massachusetts offers a range of activities suitable for family vacations. The town is known for its proximity to soccer fields, making it perfect for families who enjoy the sport. There are also plenty of family-friendly attractions, such as wildlife and birdwatching spots, where you can explore nature together. Winchester is also close to business districts, making it convenient for working parents. Additionally, the town offers opportunities for hunting and enjoying beautiful flowers. Don't miss popular landmarks like the Statue of Liberty and Massachusetts Avenue during your visit to Winchester.

  1. Winter Pond: Winter Pond is a picturesque lake nestled in Winchester. This point of interest is known for its stunning scenery, surrounded by lush greenery and towering skyscrapers. It offers a range of outdoor activities, including water sports like kayaking and paddleboarding. The calm and serene atmosphere of Winter Pond makes it a perfect spot for a romantic getaway. You can also explore the historical architecture in the area and enjoy the friendly ambiance of the nearby university. After a day of outdoor adventure, indulge in dining at the charming restaurants nearby or immerse yourself in the local art scene. Winter Pond is the ideal destination for those seeking a mix of romance, scenery, and outdoor experiences.

Where to stay in Winchester

Experience the charm of Winchester, Massachusetts on your family vacation. Located just a short drive from downtown Boston, this hidden gem offers a peaceful retreat from the hustle and bustle of the city. Explore the beautiful nature trails and go birdwatching at the nearby lake, perfect for outdoor enthusiasts. Take a leisurely stroll through the town's quaint streets and discover its rich history and charming shops. For sports lovers, catch a soccer game at one of the local fields. Winchester offers a perfect blend of small-town charm and convenient access to the vibrant city of Boston.

  1. Boston: Boston is a popular multi-city vicinity located 7.5 miles away from Winchester. It is known for its rich historical significance, world-renowned museums, urban atmosphere, and prestigious universities. Families can explore the city's historical sites, visit fascinating museums, and enjoy various sports activities. They can also take guided tours to learn about the city's architecture, theater scene, and iconic monuments. With its impressive skyscrapers and vibrant atmosphere, Boston offers a unique blend of history and modernity that is sure to captivate visitors of all ages.
  2. Salem: Salem, situated 13.1 miles away from Winchester, is a city famous for its historical importance and captivating architecture. Families can delve into the city's rich history by visiting its museums and exploring the charming streets on foot. They can also enjoy shopping and dining experiences in Salem's unique establishments. The friendly locals and welcoming atmosphere make it an ideal destination for a family vacation. Additionally, Salem is known for its spooky folklore, making it a fascinating place to learn about witch trials and other historical events.
  3. Cambridge: Located just 5.6 miles away from Winchester, Cambridge is a vibrant city known for its prestigious university and cultural offerings. Families can visit world-class museums, admire the urban architecture, and enjoy the scenic views of the river. Cambridge offers a variety of dining options, sports activities, and shopping opportunities. The city's artistic scene and running trails provide additional attractions for visitors of all ages. With its blend of intellectual atmosphere and recreational opportunities, Cambridge offers a unique experience that will appeal to the whole family.

Best times to go to Winchester

The travel seasons of Winchester

Trips to Winchester show no change in popularity throughout the year. The peak season to visit is from April to June, with April being the highest month. Off-peak season starts from October to December, and November sees the least travelers.

Winchester has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 73.6 degrees Fahrenheit. The wettest month in Winchester is December, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January28.6°F (-1.9°C)Light RainMostly Sunny
February29.8°F (-1.2°C)Light RainMostly Cloudy
March36.9°F (2.7°C)Light RainMostly Sunny
April47.7°F (8.7°C)Light RainMostly Sunny
May58.3°F (14.6°C)Light RainMostly Sunny
June66.4°F (19.1°C)Light RainMostly Sunny
July73.6°F (23.1°C)Light RainMostly Sunny
August72.3°F (22.4°C)Light RainMostly Sunny
September65.3°F (18.5°C)Light RainMostly Sunny
October54.9°F (12.7°C)Light RainMostly Sunny
November43.3°F (6.3°C)Light RainMostly Sunny
December35.1°F (1.7°C)Light RainMostly Sunny

Food and dining in Winchester

When visiting Winchester, Massachusetts, you'll find a variety of mouthwatering cuisines to satisfy your food cravings. One popular choice is China Sky, a highly rated Asian Chinese restaurant known for its authentic flavors. If you're in the mood for pizza, Andrea's Pizza is a must-visit, offering delicious pies in a cozy atmosphere. Another top option is Gloria's Pizzeria, a Mediterranean Italian restaurant that will transport you to the flavors of the Mediterranean. Whether you're looking for a romantic dinner or a hot cup of coffee, Winchester has a diverse array of restaurants to satisfy your taste buds.

How do I find a great hotel with Travelocity?

Ensure your entire crew has an unforgettable vacation. When looking for the ideal accommodations, utilize the family-friendly badge to uncover hotels that offer additional amenities for children. Moreover, our bespoke filters assist in narrowing down hotels near prominent attractions, providing enhanced cleaning and falling within your budget range.

Why should I book with Travelocity?

Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide stress-free travel every time you and your family book with us so that you can spend less time worrying and more time creating cherished memories. To that end, we will assist you in finding and organizing your ideal trip, as well as offering transparent pricing and reliable reviews, along with 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Winchester?

Save money on your trip to Winchester, Massachusetts by visiting during the less popular season from October to December. Consider bundling your flights, hotel, and car bookings together to take advantage of discounted prices. While in Winchester, enjoy inexpensive local activities such as birdwatching, exploring the beautiful lakes and nature, and visiting family-friendly sports facilities. These affinities offer affordable entertainment options for you and your family to enjoy while saving on your travel expenses.

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 $176. 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 3,740 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

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

5 out of 5
Posted 17 hours ago
Travelocity Verified Review
"Small but very clean room. The bed was incredibly comfortable. Friendly staff at the front desk. "
A verified traveler from Acushnet stayed at Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity