Search Guest Houses in Winthrop

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Guest Houses in Winthrop

Premium bedding, down comforters, minibar, individually decorated
Clarendon Square

Clarendon Square

4.0 star property
South End
9.2 out of 10, Wonderful, (249)
"In a word: charming"
United States
David
$229 nightly
The price is $263
Dec 4 - Dec 5
Total with taxes and fees
Clarendon Square
Property entrance
Copley House

Copley House

3.0 star property
Back Bay
9.0 out of 10, Wonderful, (1917)
"Fantastic place to stay and visit Boston."
United States
Poorvajan
$112 nightly
The price is $129
Dec 10 - Dec 11
Total with taxes and fees
Copley House
Exterior
Oasis Guest House

Oasis Guest House

2.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (1386)
"Lovely stay! "
United States
Hilary
$121 nightly
The price is $139
Dec 15 - Dec 16
Total with taxes and fees
Oasis Guest House
Fridge, microwave, oven, dishwasher
184 Heath St

184 Heath St

2.0 star property
Jamaica Plain
3.4 out of 10, (40)
"👍"
United States
Musa
$103 nightly
The price is $118
Dec 4 - Dec 5
Total with taxes and fees
184 Heath St
Front of property
ESJACPE GUEST HOUSE

ESJACPE GUEST HOUSE

2.0 star property
Jamaica Plain
2.8 out of 10, (27)
"Thanks I liked my stay"
United States
Kristina
$149 nightly
The price is $171
Dec 4 - Dec 5
Total with taxes and fees
ESJACPE GUEST HOUSE
King Room @ 1087 Beacon St. | Desk, iron/ironing board, free WiFi, alarm clocks
Beacon Inn 1087

Beacon Inn 1087

2.5 star property
Longwood
8.0 out of 10, Very Good, (778)
"Staff was the best, led me directly to where to park and upgraded me to another room available. The room was extremely spacious with a nice tv and fireplace. The property appears to be a former home divided and has a very homely feel. Stayed one night to attend an event nearby, and was able to leave my car to take public transit to and from the event. "
United States
Kyle
$109 nightly
The price is $122
Dec 4 - Dec 5
Total with taxes and fees
Beacon Inn 1087
Exterior detail
Coolidge Corner Guest House

Coolidge Corner Guest House

3.5 star property
Coolidge Corner South Side
8.2 out of 10, Very Good, (625)
"Very pleasant, comfortable stay. "
United States
Valerie
$125 nightly
The price is $140
Jan 1 - Jan 2, 2026
Total with taxes and fees
Coolidge Corner Guest House
Double Room with One Double Bed @ 1750 Beacon St | Desk, iron/ironing board, free WiFi, bed sheets
Beacon Inn 1750

Beacon Inn 1750

3.0 star property
Brookline
7.4 out of 10, Good, (757)
"A little older but great location and very nice staff. "
Canada
Marc
$109 nightly
The price is $122
Dec 4 - Dec 5
Total with taxes and fees
Beacon Inn 1750
Standard Double Room, 1 Double Bed, Shared Bathroom | Private kitchen | Fridge, microwave, oven, stovetop
Tranquil House in Cambridge

Tranquil House in Cambridge

3.0 star property
Strawberry Hill
8.8 out of 10, Excellent, (158)
"Is very quiet and very clean "
Mexico
ALEJANDRO
$95 nightly
The price is $109
Dec 4 - Dec 5
Total with taxes and fees
Tranquil House in Cambridge
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.
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Top Winthrop Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Staff was very friendly and helpful. Rooms were clean and new. "
Rosemarie 3-night trip
Posted 2 days ago
Omni Boston Hotel at the Seaport

Find out more about Winthrop

Winthrop Guest Houses information

Number of reviews
5,559
Accommodation
16 Guest Houses
Lowest Price
$109
Highest Price
$263

Frequently asked questions

What is the nightly rate for a guest house in Winthrop?
Rates for Winthrop guest houses vary, but travelers can find great-value prices from $109 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winthrop guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Winthrop guest house and a B&B?
A guest house in Winthrop is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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