Search Guest Houses in Winchester from CA $88

  • 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
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Winchester guest houses

A bedroom with a bed, a desk, and a chair.

1. Tranquil House in Cambridge

Tranquil House in Cambridge
3.0 star property
Strawberry Hill
8.8 out of 10, Excellent, (192 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 $160
CA $183 total
includes taxes & fees
Nov 15 - Nov 16
Tranquil House in Cambridge
A bedroom with a bed, a red chair, a small table with a book, a potted plant, and a staircase leading to an outdoor area.

2. Cambridge Common House

Cambridge Common House
4.0 star property
West Cambridge
10.0 out of 10, Exceptional, (61 reviews)
"The place was delightful, well located and FUN!"
United States
stacie
The price is CA $257
CA $294 total
includes taxes & fees
Nov 29 - Nov 30
Cambridge Common House
A building with a brick facade partially covered in green ivy.

3. Copley House

Copley House
3.0 star property
Back Bay
9.2 out of 10, Wonderful, (2,329 reviews)
"Great location"
United States
Sam
The price is CA $160
CA $184 total
includes taxes & fees
Nov 25 - Nov 26
Copley House
A historic brick building with a prominent 'Breckinridge Inn' sign, a stone staircase, and a large window.

4. Beacon Inn 1750

Beacon Inn 1750
3.0 star property
Brookline
7.6 out of 10, Good, (821 reviews)
"Excellent location, close to great food ,best bagels in Brookline (mamalehs), and superb tacos (bartaco), easy access to T."
United States
Sharon
The price is CA $153
CA $171 total
includes taxes & fees
Dec 1 - Dec 2
Beacon Inn 1750
A row of blue townhouses with a porch and a sign for 'Boutique Inn'.

5. Ginkgo House on Harvard

Ginkgo House on Harvard
3.0 star property
Central Square
9.8 out of 10, Exceptional, (87 reviews)
"The staff was great and were very attentive and always eager to help with a smile. The rooms were comfortable and clean. Parking available upon request. Location was very good. No TV's which is fine, just make sure to have a device your children if needed. We do recommend and we will stay there again."
United States
Adam
The price is CA $291
CA $333 total
includes taxes & fees
Nov 29 - Nov 30
Ginkgo House on Harvard
A red brick building with multiple windows, a prominent entrance with a door, and a small porch area with potted plants.

6. Beacon Inn 1087

Beacon Inn 1087
2.5 star property
Longwood
8.0 out of 10, Very good, (888 reviews)
"Super smooth check in and rooms were very clean and nice"
United States
Renee
The price is CA $153
CA $171 total
includes taxes & fees
Dec 1 - Dec 2
Beacon Inn 1087
A row of yellow brick townhouses with a central entrance, large windows, and a tree in the foreground.

7. Oasis Guest House

Oasis Guest House
2.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (1,554 reviews)
"Great location , clean rooms and lovely breakfast"
Canada
Phillip Danny
The price is CA $151
CA $174 total
includes taxes & fees
Nov 22 - Nov 23
Oasis Guest House
A two-story house with a green exterior and white trim, featuring a porch with a purple railing and a small garden area with plants and a planter.

8. Coolidge Corner Guest House

Coolidge Corner Guest House
3.5 star property
Coolidge Corner
8.4 out of 10, Very good, (665 reviews)
"Wonderful little Inn Wish the room rate wasn’t so high… Internet was out my entire stay but the staff were very accommodating with directions & hot spot. No TV which was a bummer but def recommend this place. Fun little breakfast nook with great coffee & bagels."
United States
ellen
The price is CA $167
CA $186 total
includes taxes & fees
Nov 30 - Dec 1
Coolidge Corner Guest House
A hotel room with a bed, bedside lamps, a mirror, a small desk with a coffee maker, and a motivational quote on the wall.

9. RENU on Tremont

RENU on Tremont
2.0 star property
South End
The price is CA $159
CA $314 total
includes taxes & fees
Dec 8 - Dec 9
RENU on Tremont
A bedroom with a large bed, a fireplace, two windows with blinds, a chandelier, and a side table with a lamp.

10. Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.4 out of 10, (393 reviews)
"Was perfect for a brief stay. The amenities were appropriate for the price and check-in /check-out was very easy and convenient"
United States
Benjamin
The price is CA $114
CA $203 total
includes taxes & fees
Dec 2 - Dec 3
Bay Village Suites
A kitchen with wooden cabinets, a white stove, and a microwave.

11. 184 Heath St

184 Heath St
2.0 star property
Jamaica Plain
3.4 out of 10, (100 reviews)
"The room was ok. Wish bathroom was a little cleaner but overall decent for a short stay"
United States
Daniela
The price is CA $88
CA $187 total
includes taxes & fees
Dec 2 - Dec 3
184 Heath St
A bedroom with a large clawfoot bathtub, a four-poster bed, and a wooden ceiling.

12. Silsbee's by Daniels House

Silsbee's by Daniels House
4.0 star property
Salem
9.6 out of 10, Exceptional, (93 reviews)
"Very charming place to stay."
United States
Amy
The price is CA $276
CA $309 total
includes taxes & fees
Dec 2 - Dec 3
Silsbee's by Daniels House
A city skyline at night with illuminated buildings.

13. Clarendon Square

Clarendon Square
4.0 star property
South End
9.6 out of 10, Exceptional, (261 reviews)
"This is a beautiful property with clean, comfortable rooms. It is on a very quiet street, and the pillows and bedding are perfect, for a great night's sleep. The location is very good, and close to many quality restaurants and shops etc. Stephen is a great host, very helpful, and a pleasure to chat with. Highly recommended."
United States
Darron
The price is CA $384
CA $463 total
includes taxes & fees
Nov 8 - Nov 9
Clarendon Square
A house with a pond in front, surrounded by autumn-colored trees.

14. The Inn on the Horse Farm

The Inn on the Horse Farm
3.0 star property
Sudbury
8.0 out of 10, Very good, (288 reviews)
"well maintained, beautiful Tv kept buffering-- that cannot happen no toilet or sink in room"
United States
Steven
The price is CA $229
CA $256 total
includes taxes & fees
Dec 8 - Dec 9
The Inn on the Horse Farm
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

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
An aerial view of a town with a lake, church steeples, and a bridge.

Top reviews in Winchester

A bedroom with a bed, a red chair, a small table with a book, a potted plant, and a staircase leading to an outdoor area.
Cambridge Common House

Cambridge Common House

Cambridge Common House
West Cambridge

10/10 Excellent

Well located close to harvard square, very clean, quiet, cozy and very welcoming staff and entire experience; rooms with the little patios are excellent; breakfast looked excellent ( but could not enjoy as i had meetings outside every day before 8am, when breakfast starts)
Canada
christian
Reviewed October 10, 2026
Cambridge Common House

Explore a world of travel with Expedia