Search Guest Houses in Winthrop

  • 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
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winthrop guest houses

A building with a brick facade partially covered in green ivy.

1. Copley House

Copley House
3.0 star property
Back Bay
9.2 out of 10, Wonderful, (2,332 reviews)
"Great location"
United States
Sam
The price is Rp2.194.533
Rp2.522.616 total
includes taxes & fees
25 Nov - 26 Nov
Copley House
A row of yellow brick townhouses with a central entrance, large windows, and a tree in the foreground.

2. 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 Rp1.950.696
Rp2.242.325 total
includes taxes & fees
24 Nov - 25 Nov
Oasis 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.

3. RENU on Tremont

RENU on Tremont
2.0 star property
South End
The price is Rp1.625.580
Rp3.561.239 total
includes taxes & fees
12 Nov - 13 Nov
RENU on Tremont
A red brick building with multiple windows, a prominent entrance with a door, and a small porch area with potted plants.

4. Beacon Inn 1087

Beacon Inn 1087
2.5 star property
Longwood
8.0 out of 10, Very good, (890 reviews)
"Super smooth check in and rooms were very clean and nice"
United States
Renee
The price is Rp1.972.732
Rp2.203.564 total
includes taxes & fees
8 Dec - 9 Dec
Beacon Inn 1087
A bedroom with a large bed, a fireplace, two windows with blinds, a chandelier, and a side table with a lamp.

5. Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (397 reviews)
"The room was clean and had a microwave, refrigerator, iron, and toaster. Check-in and check-out were smooth."
United States
Tamara
The price is Rp1.463.022
Rp2.616.046 total
includes taxes & fees
7 Dec - 8 Dec
Bay Village Suites
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.

6. 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 Rp2.986.733
Rp3.418.316 total
includes taxes & fees
24 Nov - 25 Nov
Cambridge Common House
A bedroom with a bed, a desk, and a chair.

7. 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 Rp2.131.316
Rp2.439.291 total
includes taxes & fees
15 Nov - 16 Nov
Tranquil House in Cambridge
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, (666 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 Rp1.968.758
Rp2.199.049 total
includes taxes & fees
9 Dec - 10 Dec
Coolidge Corner Guest House
A historic brick building with a prominent 'Breckinridge Inn' sign, a stone staircase, and a large window.

9. 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 Rp1.972.732
Rp2.203.564 total
includes taxes & fees
7 Dec - 8 Dec
Beacon Inn 1750
A row of blue townhouses with a porch and a sign for 'Boutique Inn'.

10. 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 Rp3.670.397
Rp4.200.768 total
includes taxes & fees
30 Nov - 1 Dec
Ginkgo House on Harvard
A bedroom with a large clawfoot bathtub, a four-poster bed, and a wooden ceiling.

11. 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 Rp3.797.063
Rp4.241.319 total
includes taxes & fees
7 Dec - 8 Dec
Silsbee's by Daniels House
A kitchen with wooden cabinets, a white stove, and a microwave.

12. 184 Heath St

184 Heath St
2.0 star property
Jamaica Plain
3.4 out of 10, (101 reviews)
"The overall experience felt nice. had a great time cooking for my family in this very functional kitchen. The dishes I made were loved by the whole family. Very good times at 184 Heath Street !"
Canada
Leo
The price is Rp1.137.906
Rp2.408.425 total
includes taxes & fees
8 Dec - 9 Dec
184 Heath St
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 Rp5.769.115
Rp6.963.096 total
includes taxes & fees
12 Nov - 13 Nov
Clarendon Square
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 Winthrop

This coastal gem offers spectacular Boston skyline views from Deer Island and Belle Isle Marsh Reservation. Enjoy fresh seafood at waterfront restaurants or relax on Winthrop Beach when summer temperatures rise.

See all hotels in Winthrop
A coastal town with a prominent lighthouse on a hill, surrounded by houses and greenery.

Top reviews in Winthrop

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

Beautifully designed rooms, impeccable service, and really great location. Loved Cambridge Common House - I think the best hotel option in Harvard Square at the moment, and a really great addition to the area.
United Kingdom
Omolola
Reviewed October 15, 2026
Cambridge Common House