20 Best B&B in Winthrop, MA - Bed and Breakfast from $86

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

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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

Winthrop

Jodi

$189 nightly

Nov 1 - Nov 2

Total with taxes and fees

2. Homestay BnB Near Downtown Boston

Dorchester

Uyen Thi Minh

$80 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

3. Homestay In Boston -

Dorchester

Dhruv

$75 nightly

Nov 16 - Nov 17

Total with taxes and fees

A kitchen with a stainless steel stove, oven, microwave, and refrigerator.

4. Homestay In Fields Corner Area Boston

Dorchester

Abhinav

$86 nightly

Nov 14 - Nov 15

Total with taxes and fees

A spacious room with a large window, a dark blue sofa, and a wooden floor.

5. Homestay Near Near Savin Hill Area

Dorchester

Gaby

$84 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with white cabinets, a marble island, and pendant lighting.

6. Homestay Near Downtown Boston

Dorchester

Alexander Joshua

$119 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Hull

Maximiliano

$199 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

Brighton

L M C.

$150 nightly

Oct 22 - Oct 23

Total with taxes and fees

A two-story building with a sign reading "Irving House Bed & Breakfast".

9. Irving House At Harvard

Mid-Cambridge

Ellen

$215 nightly

Oct 25 - Oct 26

Total with taxes and fees

A living room with a sectional sofa, a glass coffee table, a small round table, and a wall-mounted TV.

10. Charming B&B close to Salem and Boston

Lynn

Maria

$195 nightly

Oct 19 - Oct 20

Total with taxes and fees

11. The Salem Inn

Salem

Donald

$229 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

Back Bay

Leighton

$349 nightly

Nov 1 - Nov 2

Total with taxes and fees

A residential house with a porch, two wooden doors, a black railing, and a number '8' on the wall.

13. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

Lynn

$343 nightly

Oct 18 - Oct 19

Total with taxes and fees

A garden with a flower in the foreground and a row of houses in the background.

14. The Inn At Scituate Harbor

Scituate

robert

$209 nightly

Nov 2 - Nov 3

Total with taxes and fees

A two-story building with a red door and multiple windows.

15. Daniels House Inn

Salem

Kristofor

$259 nightly

Nov 17 - Nov 18

Total with taxes and fees

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Top Winthrop Hotel Reviews

The Revolution Hotel

8/10 Good

"The bed was very comfortable. Staff responsive. The shared bathrooms were manageable. Just had to be organized."

Seaport Hotel Boston

8/10 Good

"The location of this hotel was ideal for our visit. We planned a 2-day pre-cruise stay on our own. It's easy to take an Uber, taxi or Silver Line bus to the Flynn cruise port from this hotel. The room was comfortable, nicely appointed and had great western views over a park. It was quiet. The food in the dining room was tasty - some of the best clam chowder we've tasted. If you like martinis, try the chocolate espresso! Yum. My only complaint, and it was a big misstep - we had a fire alarm at almost midnight one night of our stay. It was a cluster. No staff anywhere. Our stairwell emptied into staff/office hallway and the security guard (who worked there) also didn't know what was going on when we asked. We got more help from the firefighters as they were leaving the site. It was apparently a false alarm, but after you make your guests walk down many flights of stairs, you'd think you'd post up staff to advise the very sleepy and confused patrons where to go and make sure we knew what to do. Nobody in the lobby knew what was going on. Some manager advised us we could return to our rooms thru the elevators, but when loads of people tried to use the elevators, they were still out of service. After waiting a while, we walked up 7 flights of stairs, but the stairway we took was not straight up. We got lost in the conference side of the hotel. I think they need to do some more practice drills. It was a disappointing end to an otherwise nice stay."

citizenM Boston Back Bay

10/10 Excellent

"Great location! Hotel was close to shops and restaurants. The interior is super cute with a retro vibe. The room was clean and the bed was decent. Front desk staff was very friendly and helpful. The only negative experience was the waitstaff at the bar. Both nights they showed their annoyance when asking for service because it was near closing time."

Hyatt Regency Boston

10/10 Excellent

"Location was great for walking the city. Parking was quite expensive but attached to hotel. The arrangement of the elevators and location of the lobby and pool/workout room was confusing. Room was clean and nice size. Great decor and modern design. Staff was friendly and extremely helpful on visiting the city. Ate at hotel restaurant—excellent."

Find out more about Winthrop

Winthrop B&B information

Number of reviews	2,729
Accommodation	38 B&B
Lowest Price	$86
Highest Price	$401

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 $86 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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Our top choices for Winthrop bed & breakfast

1. Château sur Mer Bed & Breakfast

2. Homestay BnB Near Downtown Boston

3. Homestay In Boston -

4. Homestay In Fields Corner Area Boston

5. Homestay Near Near Savin Hill Area

6. Homestay Near Downtown Boston

7. The Beacon Waterfront Inn

8. The Pistachio Room at TPH - Boston

9. Irving House At Harvard

10. Charming B&B close to Salem and Boston

11. The Salem Inn

12. The College Club of Boston

13. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

14. The Inn At Scituate Harbor

15. Daniels House Inn

Top Winthrop Hotel Reviews

The Revolution Hotel

The Midtown Hotel MOD Collection by Sonesta

Wyndham Boston Beacon Hill

Harborside Inn Of Boston

The Dagny Boston

Arcadian Hotel

Seaport Hotel Boston

citizenM Boston Back Bay

Hyatt Regency Boston

Find out more about Winthrop

Winthrop B&B information

Frequently asked questions

Explore a world of travel with Expedia

Book Winthrop Bed & Breakfast

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Winthrop bed & breakfast

1. Château sur Mer Bed & Breakfast

2. Homestay BnB Near Downtown Boston

3. Homestay In Boston -

4. Homestay In Fields Corner Area Boston

5. Homestay Near Near Savin Hill Area

6. Homestay Near Downtown Boston

7. The Beacon Waterfront Inn

8. The Pistachio Room at TPH - Boston

9. Irving House At Harvard

10. Charming B&B close to Salem and Boston

11. The Salem Inn

12. The College Club of Boston

13. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

14. The Inn At Scituate Harbor

15. Daniels House Inn

Top Winthrop Hotel Reviews

The Revolution Hotel

Find out more about Winthrop

Winthrop B&B information

Frequently asked questions

Explore a world of travel with Expedia