Find Boutique Hotels in Winchester, MA from $154

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

Check availability on Winchester Boutique Hotels

Top Winchester Boutique Hotels

Exterior
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4.0 star property
8.6 out of 10, Excellent, (3883)
"Great hotel, great location, great staff! "
Armen
$132 nightly
The price is $154
Nov 9 - Nov 10
Total with taxes and fees
Copley Square Hotel, a FOUND Hotel
Peruvian cuisine
The Godfrey Hotel Boston
The Godfrey Hotel Boston
4.0 star property
9.4 out of 10, Exceptional, (4535)
"Great hotel in a great location."
Michael J.
$237 nightly
The price is $276
Nov 16 - Nov 17
Total with taxes and fees
The Godfrey Hotel Boston
Interior
Staypineapple, A Delightful Hotel, South End
Staypineapple, A Delightful Hotel, South End
3.0 star property
8.8 out of 10, Excellent, (1011)
"Cute room, kind staff, great location."
Loren
$174 nightly
The price is $202
Nov 16 - Nov 17
Total with taxes and fees
Staypineapple, A Delightful Hotel, South End
Front of property
Hotel AKA Boston Common
Hotel AKA Boston Common
4.0 star property
9.0 out of 10, Wonderful, (1333)
"Great staff and location"
Carlton
$275 nightly
The price is $320
Oct 31 - Nov 1
Total with taxes and fees
Hotel AKA Boston Common
Terrace/patio
Hotel Commonwealth
Hotel Commonwealth
4.5 star property
9.4 out of 10, Exceptional, (1796)
"Great stay !"
Donna
$243 nightly
The price is $283
Nov 16 - Nov 17
Total with taxes and fees
Hotel Commonwealth
View from room
The Bostonian Boston
The Bostonian Boston
4.0 star property
8.4 out of 10, Very Good, (1961)
"The hotel was in a great walking location to many sites and restaurants."
rob
$179 nightly
The price is $208
Nov 16 - Nov 17
Total with taxes and fees
The Bostonian Boston
Exterior
Pennyweight Hotel Boston, Curio Collection by Hilton
Pennyweight Hotel Boston, Curio Collection by Hilton
4.0 star property
8.2 out of 10, Very Good, (1135)
"Super close to TD garden, friendly service beautiful rooms "
Heather
$208 nightly
The price is $242
Nov 16 - Nov 17
Total with taxes and fees
Pennyweight Hotel Boston, Curio Collection by Hilton
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
The Colonnade Hotel Back Bay
The Colonnade Hotel Back Bay
4.0 star property
9.2 out of 10, Wonderful, (2226)
"Great stay!"
Alisa
$311 nightly
The price is $362
Oct 30 - Oct 31
Total with taxes and fees
The Colonnade Hotel Back Bay
Aerial view
The Hotel Marblehead
The Hotel Marblehead
3.5 star property
9.2 out of 10, Wonderful, (423)
"Loved our stay."
Christopher
$176 nightly
The price is $197
Nov 17 - Nov 18
Total with taxes and fees
The Hotel Marblehead
Reception
Eurostars The Boxer
Eurostars The Boxer
4.0 star property
8.6 out of 10, Excellent, (1328)
"I like the small cozy property and convenience to walk to a lot of bars and restaurants "
James
$237 nightly
The price is $276
Nov 17 - Nov 18
Total with taxes and fees
Eurostars The Boxer
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

Top Winchester Hotel Reviews

The Newbury Boston

The Newbury Boston

10/10 Excellent
"Great"
JEANPAUL 1-night trip
Posted 1 day ago
The Newbury Boston

Frequently asked questions

What's there to see and do in Winchester?
After you've decided where to stay in family-friendly Winchester, figure out some fun things to do on your trip. Major sights and activities around Winchester include TD Garden, Fenway Park, and New England Aquarium. While you're here, make sure you don't miss Encore Boston Harbor, Harvard Square, and Boston Harbor.
What kind of weather should I plan for when I travel to Winchester?
Understanding the weather in Winchester will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What's the best way to get to my boutique hotel in Winchester?
You have a few options for getting to and around Winchester. The closest major airport is Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) from the heart of the city, but Boston, MA (BNH-Boston Harbor Seaplane Base) may also be an option. To see more of the surrounding area, ride one of the trains from Winchester Station or Winchester Wedgemere Station.

Explore a world of travel with Expedia