A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Search Guest Houses in Winchester from CA $182

  • 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

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Winchester guest houses

Superior Room, 2 Bedrooms, Non Smoking, Connecting Rooms

1. Tranquil House in Cambridge

Tranquil House in Cambridge
3.0 star property
Strawberry Hill
8.8 out of 10, Excellent, (176 reviews)
"Responsive owner, easy to find with maps, easy parking out front- very clean and efficient so so quiet!!"
United States
Lisa
The price is CA $159
CA $182 total
includes taxes & fees
Aug 23 - Aug 24
Tranquil House in Cambridge
Property entrance

2. Copley House

Copley House
3.0 star property
Back Bay
9.2 out of 10, Wonderful, (2,260 reviews)
"Great property and excellent staff."
United States
Arunesh C
The price is CA $272
CA $313 total
includes taxes & fees
Aug 30 - Aug 31
Copley House
Exterior

3. Oasis Guest House

Oasis Guest House
2.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (1,513 reviews)
"Great location, lovely host."
United States
Megan Elizabeth Rubiner
The price is CA $215
CA $247 total
includes taxes & fees
Aug 26 - Aug 27
Oasis Guest House
Desk, laptop workspace, WiFi (free), bed sheets

4. Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (343 reviews)
"Good price for the convenience of the location. Not glamorous at all. Pictures make it look a little better than what it actually is"
United States
Daniel
The price is CA $135
CA $227 total
includes taxes & fees
Aug 27 - Aug 28
Bay Village Suites
Exterior

5. Beacon Inn 1750

Beacon Inn 1750
3.0 star property
Brookline
7.4 out of 10, Good, (799 reviews)
"The property was on a well lit roadway in Brookline with quick access to the Greenline and other nearby services."
United States
Chad
The price is CA $193
CA $216 total
includes taxes & fees
Aug 24 - Aug 25
Beacon Inn 1750
Petite Queen with private Patio

6. Cambridge Common House

Cambridge Common House
4.0 star property
West Cambridge
10.0 out of 10, Exceptional, (32 reviews)
"It’s a pretty nice place to stay."
United States
Jason
The price is CA $335
CA $383 total
includes taxes & fees
Aug 27 - Aug 28
Cambridge Common House
Front of property

7. Ginkgo House on Harvard

Ginkgo House on Harvard
3.0 star property
Central Square
9.8 out of 10, Exceptional, (81 reviews)
"Excellent little hotel"
United States
said
The price is CA $352
CA $403 total
includes taxes & fees
Aug 30 - Aug 31
Ginkgo House on Harvard
King Room @ 1087 Beacon St.

8. Beacon Inn 1087

Beacon Inn 1087
2.5 star property
Longwood
8.0 out of 10, Very good, (855 reviews)
"Amazing location, large rooms, friendly staff!"
United States
Stacy
The price is CA $219
CA $244 total
includes taxes & fees
Aug 27 - Aug 28
Beacon Inn 1087
Property entrance

9. Coolidge Corner Guest House

Coolidge Corner Guest House
3.5 star property
Coolidge Corner
8.2 out of 10, Very good, (652 reviews)
"The staff was all spectacular and the rooms were so cute and clean. The breakfast was smaller than I imagined but still great. Everything felt safe and cozy. And using the laundry machines was free which was way better than a hotel!!"
United States
Joy
The price is CA $213
CA $238 total
includes taxes & fees
Aug 25 - Aug 26
Coolidge Corner Guest House
Fridge, microwave, oven, dishwasher

10. 184 Heath St

184 Heath St
2.0 star property
Jamaica Plain
3.4 out of 10, (66 reviews)
"Shared bath (not mentioned in the description) Room has no towels, pillows. Ghetto place."
United States
Maneesh
The price is CA $115
CA $216 total
includes taxes & fees
Aug 29 - Aug 30
184 Heath St
Classic Room

11. ESJACPE GUEST HOUSE

ESJACPE GUEST HOUSE
2.0 star property
Jamaica Plain
2.8 out of 10, (29 reviews)
"Thanks I liked my stay"
United States
Kristina
The price is CA $242
CA $403 total
includes taxes & fees
Aug 29 - Aug 30
ESJACPE GUEST HOUSE
Property grounds

12. The Inn on the Horse Farm

The Inn on the Horse Farm
3.0 star property
Sudbury
8.0 out of 10, Very good, (279 reviews)
"I could not find the hotel, arriving late at night, and when I called the listed number for assistance in finding it, there was no answer...at all. So I slept in my car."
United States
William
The price is CA $246
CA $274 total
includes taxes & fees
Sep 9 - Sep 10
The Inn on the Horse Farm
Romantic Room

13. Silsbee's by Daniels House

Silsbee's by Daniels House
4.0 star property
Salem
9.6 out of 10, Exceptional, (89 reviews)
"Great"
United States
John
The price is CA $365
CA $408 total
includes taxes & fees
Aug 30 - Aug 31
Silsbee's by Daniels House
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

Top Winchester Hotel Reviews

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Great hotel but the rooms are amall"
Ron 12-night trip
Posted less than an hour ago
citizenM Boston North Station

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
3,171
Accommodation
19 Guest Houses
Lowest Price
CA $182
Highest Price
CA $408

Explore a world of travel with Expedia