A coastal town with a lighthouse, sandy beach, and residential buildings.

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Winthrop bed & breakfast

A hotel room with a bed, a desk with a lamp, a TV, and a map on the wall.

1. Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.8 out of 10, Excellent, (226 reviews)
"I loved this place. She was so welcoming and accommodating. It was a wonderful time!!"
United States
Lisa
$195 nightly
The price is $218
Oct 25 - Oct 26
Total with taxes and fees
Château sur Mer Bed & Breakfast
A kitchen with a stainless steel stove, oven, microwave, and refrigerator.

2. Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
7.8 out of 10, Good, (84 reviews)
"Great property, the hosts are very helpful. The property also had things in fridge for breakfast"
United States
Abhinav
$127 nightly
The price is $146
Sep 29 - Sep 30
Total with taxes and fees
Homestay In Fields Corner Area Boston
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

3. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.0 out of 10, Very good, (104 reviews)
"Great stay for dilli travelers good location with connectivity and house was clean and well equipped."
United States
Dhruv
$107 nightly
The price is $123
Oct 1 - Oct 2
Total with taxes and fees
Homestay In Boston -
A modern kitchen with white cabinets, a marble island, and pendant lighting.

4. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (56 reviews)
"Really clean space with a cozy vibe. Everything worked for us during the stay and the location was convenient. The walls were super thin so sound definitely travels but overall a safe, and comfy stay!"
Canada
Meagan
$115 nightly
The price is $132
Oct 1 - Oct 2
Total with taxes and fees
Homestay Near Downtown Boston
A spacious room with a large window, a dark blue sofa, and a wooden floor.

5. Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (61 reviews)
"God value for money, close to subway"
United Kingdom
Daniel
$120 nightly
The price is $138
Oct 1 - Oct 2
Total with taxes and fees
Homestay Near Near Savin Hill Area
A living room with a sectional sofa, a glass coffee table, a small round table, and a wall-mounted TV.

6. Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston
Lynn
5.8 out of 10, (19 reviews)
"Inexpensive and close to many attractions. "
United States
Maria
$190 nightly
The price is $208
Sep 30 - Oct 1
Total with taxes and fees
Charming B&B close to Salem and Boston
A bedroom with a large bed, a nightstand, a window with blinds, a balcony with a view, and a ceiling with a skylight.

7. The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (334 reviews)
"Pristine property with the most thoughtful host! Would not hesitate to stay here again!"
United States
james
$178 nightly
The price is $198
Oct 1 - Oct 2
Total with taxes and fees
The Beacon Waterfront Inn
A living room with a brick fireplace, a brown leather sofa, a patterned rug, and a dining area with a table and chairs.

8. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (79 reviews)
"There room and common areas were very clean neat. It was a very pleasant stay. I would stay there again."
United States
L M C.
$150 nightly
The price is $172
Oct 4 - Oct 5
Total with taxes and fees
The Pistachio Room at TPH - Boston
A sailboat on calm water during sunset.

9. Josephine's Bed & Breakfast

Josephine's Bed & Breakfast
3.0 star property
Hull
9.6 out of 10, Exceptional, (134 reviews)
"Josephines was lovely. Very nostalgic, loved the decor!!! Breakfast was excellent! I am hoping to stay there again"
United States
Marsha
$164 nightly
The price is $164
Oct 15 - Oct 16
Total with taxes and fees
Josephine's Bed & Breakfast
A two-story building with a sign reading "Irving House Bed & Breakfast".

10. Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,007 reviews)
"What a wonderful experience to have stayed at Irving House. Highly recommended-"
United States
Alejandra
$315 nightly
The price is $361
Oct 12 - Oct 13
Total with taxes and fees
Irving House At Harvard
A residential house with a porch, two wooden doors, a black railing, and a number '8' on the wall.

11. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

2-bedroom bed & breakfast in adorable Lynn with AC comfort
Lynn
10.0 out of 10, Exceptional, (2 reviews)
"Michael, the host, had great communication skills and the place was clean and very accommodating. Wonderful home away from home feel. Highly recommend staying here and it’s close to Salem as well."
United States
Romualdo S.
$322 nightly
The price is $353
Sep 29 - Sep 30
Total with taxes and fees
2-bedroom bed & breakfast in adorable Lynn with AC comfort
A hotel room with a large bed, a sitting area with a table and chairs, a fireplace, and a view of the street through the windows.

12. The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.6 out of 10, Exceptional, (1,002 reviews)
"The location was brilliant."
Australia
Leighton
$429 nightly
The price is $493
Oct 27 - Oct 28
Total with taxes and fees
The College Club of Boston
A garden with a flower in the foreground and a row of houses in the background.

13. The Inn At Scituate Harbor

The Inn At Scituate Harbor
3.5 star property
Scituate
9.2 out of 10, Wonderful, (327 reviews)
"Stunning views of the harbor. Located at the edge of the downtown area, as easy walk to a number of restaurants and shops."
United States
robert
$273 nightly
The price is $299
Sep 29 - Sep 30
Total with taxes and fees
The Inn At Scituate Harbor
A two-story building with a red door and multiple windows.

14. Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (119 reviews)
"It’s a fantastic old house. Great place to stay if you’re looking for a unique experience in Salem"
Canada
Kristofor
$717 nightly
The price is $717
Oct 5 - Oct 6
Total with taxes and fees
Daniels House 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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

8/10 Good
"It was goods"
colleen 1-night trip
Posted 1 hour ago
Hyatt Regency Boston/Cambridge

Find out more about Winthrop

Winthrop B&B information

Number of reviews
3,332
Accommodation
38 B&B
Lowest Price
$123
Highest Price
$717

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 $123 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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