Find hotels in Winchester, MA from ฿2,830

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Nov - 8 Nov
Tomorrow
8 Nov - 9 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Filter by

Guest rating
Guest rating
Star rating

Top 10 Winchester hotels and places to stay

Lobby sitting area
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4.0 star property
Danvers
8.0 out of 10, Very good, (2188)
"Was a great stay."
United States
Kelly
The price is ฿3,161
฿3,531 total
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Boston North Shore
Free continental breakfast
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3.0 star property
Andover
8.2 out of 10, Very good, (1901)
"Friendly staff and nice room for the price. "
United States
Heather Steve
The price is ฿3,878
฿4,332 total
includes taxes & fees
30 Nov - 1 Dec
La Quinta Inn & Suites by Wyndham Boston-Andover
Indoor pool
Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG

2.5 star property
Chelmsford
8.8 out of 10, Excellent, (1002)
"Large clean rooms, bright nice entry area, friendly staff"
United States
Chava
The price is ฿3,434
฿3,836 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express Chelmsford by IHG
Exterior
Nantasket Beach Resort

Nantasket Beach Resort

3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1056)
"Lovely place to stay!"
United States
Patrice
The price is ฿3,860
฿4,992 total
includes taxes & fees
11 Nov - 12 Nov
Nantasket Beach Resort
Exterior
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

2.5 star property
Andover
8.8 out of 10, Excellent, (1001)
"Room was really clean and bed comfortable."
United States
Theresa
The price is ฿3,855
฿4,306 total
includes taxes & fees
1 Dec - 2 Dec
Sonesta ES Suites Andover Boston
Beach
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 star property
Beverly
9.2 out of 10, Wonderful, (1103)
"Great place to stay! Very clean and nice staff!"
United States
Shaina
The price is ฿3,674
฿4,104 total
includes taxes & fees
10 Nov - 11 Nov
The Wylie Inn and Conference Center at Endicott College
Standard Room, 1 King Bed | Premium bedding, blackout curtains, iron/ironing board, rollaway beds
Nantasket Beach Hotel

Nantasket Beach Hotel

2.5 star property
Hull
9.2 out of 10, Wonderful, (1001)
"The room was clean and the staff was very nice and resourceful upon check in. Cute little beach town restaurants within walking distance as well"
United States
Antonio
Nantasket Beach Hotel
Indoor pool
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

2.5 star property
Waltham
9.4 out of 10, Exceptional, (1493)
"The rooms were clean and the staff very courteous. "
United States
Alisbel
The price is ฿3,084
฿3,445 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn & Suites Boston/Waltham
2 restaurants, breakfast, lunch, dinner served; American cuisine
Hawthorne Hotel

Hawthorne Hotel

3.5 star property
Downtown Salem
9.4 out of 10, Exceptional, (1464)
"Beautiful hotel in an excellent location. Convenient for Salem visitors. "
United States
Emerson
Hawthorne Hotel
Terrace/patio
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3.0 star property
Tewksbury
8.8 out of 10, Excellent, (815)
"Great place. "
United States
alex
The price is ฿2,825
฿3,156 total
includes taxes & fees
4 Dec - 5 Dec
Hilton Garden Inn Tewksbury Andover
Free daily buffet breakfast
HYATT house Boston/Waltham

HYATT house Boston/Waltham

3.0 star property
Waltham
8.8 out of 10, Excellent, (1042)
"Great stay"
United States
Mason
The price is ฿3,022
฿3,376 total
includes taxes & fees
29 Nov - 30 Nov
HYATT house Boston/Waltham
Exterior
Best Western Plus Waltham Boston

Best Western Plus Waltham Boston

3.0 star property
Piety Corner
8.2 out of 10, Very good, (1075)
"Clean room, clean pool good selection of breakfast!"
United Kingdom
Jordan
The price is ฿2,855
฿3,188 total
includes taxes & fees
23 Nov - 24 Nov
Best Western Plus Waltham Boston
Exterior
Seaport Hotel Boston

Seaport Hotel Boston

4.0 star property
Seaport District
9.6 out of 10, Exceptional, (3673)
"Great location and stay!"
United States
Krithika
The price is ฿5,216
฿6,236 total
includes taxes & fees
23 Nov - 24 Nov
Seaport Hotel Boston
Billiards
Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington

4.0 star property
Burlington
9.8 out of 10, Exceptional, (1001)
"Beautiful king room Great atmosphere and vibes Super clean Alot to do nearby Bar was fun and affordable Best weekend ever"
United States
Habib
Archer Hotel Boston/Burlington
Exterior
Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

3.0 star property
Saugus
8.6 out of 10, Excellent, (1004)
"Staff was nice and room was clean"
United States
Rayna
The price is ฿3,087
฿3,448 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express Boston - Saugus by IHG
View from property
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4173)
"Great hotel! "
United States
Mark
The price is ฿4,913
฿7,046 total
includes taxes & fees
26 Nov - 27 Nov
Omni Boston Hotel at the Seaport
Deluxe Room, 2 Double Beds (Bath in Room) | 1 bedroom, premium bedding, down duvets, pillow-top beds
The Revolution Hotel

The Revolution Hotel

3.5 star property
South End
9.0 out of 10, Wonderful, (2214)
"Beautiful hotel in a quaint area of Back Bay, highly recommend. "
United States
Chad
The Revolution Hotel
Front of property – evening/night
Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington

2.0 star property
Burlington
8.8 out of 10, Excellent, (88)
"Property was conveniently situated, clean with friendly and helpful staff."
United Kingdom
Christopher
The price is ฿3,564
฿3,981 total
includes taxes & fees
9 Nov - 10 Nov
Sonesta Simply Suites Boston Burlington
Meeting facility
Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District

3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1347)
"Enjoyed my stay "
United States
JESSICA
The price is ฿3,371
฿4,868 total
includes taxes & fees
23 Nov - 24 Nov
Aloft by Marriott, Boston Seaport District
Exterior
Best Western Braintree Inn

Best Western Braintree Inn

2.5 star property
Braintree
8.2 out of 10, Very good, (1006)
"Clean room, lot of shopping and restaurants around the hotel"
United States
SARIEH ABOU
The price is ฿4,503
฿5,030 total
includes taxes & fees
14 Nov - 15 Nov
Best Western Braintree Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Winchester attractions

Winter Pond

Winter Pond offers a tranquil escape as Massachusetts' northernmost Coastal Plain Pondshore Community. Bring binoculars to spot diverse bird species while strolling along its peaceful shores.
See properties

Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

See all hotels in Winchester
Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

Top Winchester Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Great hotel "
Jennifer 1-night trip
Posted 6 hours ago
Encore Boston Harbor

More cheap stays in Winchester

Motel 6 Danvers, MA - Boston North

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North, Danvers, MA
The price is ฿2,624 per night from 10 Nov to 11 Nov
฿2,624
฿2,931 total
10 Nov - 11 Nov
includes taxes & fees
5.2/10 (1,040 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Located 8.1 mi (13 km) from the heart of Winchester, The Revolution Hotel is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Omni Boston Hotel at the Seaport and Seaport Hotel Boston. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What is staying in Winchester like?
Visitors can enjoy all that Winchester has to offer, including the football matches and lake views. TD Garden, Fenway Park and New England Aquarium are some of the top sights around the area. In Winchester, there are 3 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
A couple of favourite places to visit are Middlesex Fells Reservation and Winter Pond. Additionally, you'll find TD Garden and Fenway Park in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
How can I get around Winchester?
To venture out into the surrounding area, ride one of the trains from Winchester Station or Winchester Wedgemere Station. If you want to venture out around the area, you may want a rental car in Winchester for your journey.
What's the weather like in Winchester?
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.

Explore a world of travel with Expedia