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Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Winthrop bed & breakfast

Classic Triple Room | Interior
Homestay In Boston -

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
7.4 out of 10, Good, (3)
"Very clean and cozy"
United States
Vladimir
$77 nightly
The price is $89
Dec 24 - Dec 25
Total with taxes and fees
Homestay In Boston -
Full-size fridge, microwave, oven, stovetop
Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
9.0 out of 10, Wonderful, (6)
"The room were clean and staff was courteous. "
United States
Jonathan
$69 nightly
The price is $79
Dec 24 - Dec 25
Total with taxes and fees
Homestay In Fields Corner Area Boston
Miscellaneous
The College Club of Boston

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1004)
"Great location and beautiful building."
United States
Matthew
$169 nightly
The price is $194
Jan 1 - Jan 2, 2026
Total with taxes and fees
The College Club of Boston
Exterior detail
Irving House At Harvard

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1000)
"Clean, affordable, historic building, little libraries in every room"
United States
Josh
$105 nightly
The price is $120
Dec 24 - Dec 25
Total with taxes and fees
Irving House At Harvard
Smart TV, fireplace
The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (60)
"Great location and wonderful host"
United States
Robert M.
$150 nightly
The price is $172
Dec 24 - Dec 25
Total with taxes and fees
The Pistachio Room at TPH - Boston
King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Beacon Waterfront Inn

The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (302)
"Beautiful spacious room "
United States
Maryann
$159 nightly
The price is $178
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Beacon Waterfront Inn
Interior
Homestay Near Downtown Boston

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
4.0 out of 10, (1)
"If it weren’t for the way the host treated me, this would be a 3–4 star review. The host asks for contact via WhatsApp, which I initially thought was for convenience, but clearly it was so he could be rude outside Expedia’s visibility. I first messaged through Expedia and received no response. When I reached out on WhatsApp with a simple question about luggages, his responses were hostile. He made comments like “make your question intelligible first,” even though my message was polite and...
United States
Amanda Rasera
$77 nightly
The price is $89
Dec 24 - Dec 25
Total with taxes and fees
Homestay Near Downtown Boston
Front of property
Daniels House Inn

Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (100)
"This property is amazing. The home and rooms are clean, comfortable and beautiful. "
United States
Rachel
$225 nightly
The price is $225
Jan 16 - Jan 17, 2026
Total with taxes and fees
Daniels House Inn
Exterior
The Salem Inn

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1000)
"Johnny at breakfast was fabulous!! The two that were working with him were awesome too. Johnny recommended the pepper candy store and Turners seafood restaurant were amazing! "
United States
Donna
$180 nightly
The price is $201
Dec 26 - Dec 27
Total with taxes and fees
The Salem Inn
Front of property
North Bridge Inn

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very Good, (349)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
$195 nightly
The price is $218
Jan 1 - Jan 2, 2026
Total with taxes and fees
North Bridge Inn
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Squeaky clean room, wonderful welcome, great staff! "
Marguerite 1-night trip
Posted 9 hours ago
Harborside Inn Of Boston

Find out more about Winthrop

Winthrop B&B information

Number of reviews
3,512
Accommodation
30 B&B
Lowest Price
$79
Highest Price
$225

Frequently asked questions

What are the most popular Winthrop Bed & Breakfasts?
Château sur Mer Bed & Breakfast is a great choice for travelers seeking a unique and inviting experience in Winthrop, boasting an excellent 8.6 rating. This charming property offers a delightful partial ocean view, allowing guests to soak in the beauty of the seaside right from their accommodations. Known for its warm hospitality, guests rave about the inclusive setting and the delicious breakfast served each morning, which adds a wonderful touch to your stay.
What is the nightly rate for a Bed and Breakfast in Winthrop?
Prices for B&Bs in Winthrop often vary, but you can find a great deal from $79 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winthrop B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winthrop?
The best time to book a B&B in Winthrop is during the summer months, particularly from June to August. This is when outdoor enthusiasts flock to the area to take advantage of the pleasant weather and the stunning landscapes of the North Cascades. The vibrant energy of the season creates a friendly setting, superb for hiking, biking, and exploring the picturesque town, known for its charming Western-themed architecture.

July stands out as the most popular month, as visitors enjoy long days filled with sunshine and a wealth of activities. Temperatures typically range from the mid-50s to the low 80s Fahrenheit, allowing for comfortable outdoor adventures and leisurely strolls through town. The annual Winthrop Rhythm & Blues Festival in July adds to the lively vibe, attracting music lovers from near and far.

For those looking for a more budget-friendly option, consider visiting in September. This month offers a beautiful transition into fall, with fewer crowds and a chance to witness the changing colors of the leaves. The weather remains mild, and many outdoor activities can still be enjoyed, making it a wonderful time for scenic hikes and exploring local attractions at a more relaxed pace.
What is the difference between a Winthrop Bed & Breakfast and a hotel?
Every Winthrop B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winthrop B&Bs.

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