What is the typical weather in Winthrop, MA, and how does it affect outdoor plans?

Winthrop has a typical New England climate with four distinct seasons. Summers are warm and humid, with temperatures averaging around 25°C. Winters are cold and snowy, with temperatures often below freezing. Plan outdoor activities accordingly, as some attractions may be closed during the winter months.

What are the best bed and breakfasts in Winthrop, MA?

Among the B&Bs in Winthrop, MA, Boston Airport Subway - We're A Licensed 5* Airbnb , Shirley's Sea Breeze Airport Getaway 2 Single Beds and House By The Beach - Boston - Airport are the most popular ones.

What are the best cultural activities and events in and around Winthrop, MA?

Winthrop hosts a number of cultural events throughout the year, including the annual Winthrop Summerfest in July, which features live music, food vendors, and family-friendly activities. The town also has a vibrant arts scene, with several local galleries and studios.

What are the best bed and breakfasts with a pool in Winthrop, MA?

One Bedroom Suite In Boutique Inn , Heaven Room and Oasis Room are the best B&Bs with a pool in Winthrop, MA.

Which hiking trails are recommended for exploring in and around Winthrop, MA?

While Winthrop itself doesn't have many dedicated hiking trails, you can find some great options nearby. The 'Belle Isle Marsh Reservation' in East Boston offers a variety of trails along the waterfront, and the 'Lynn Woods Reservation' in Lynn has over 1200 acres of trails for hiking, biking, and horseback riding.

What are the best bed and breakfasts for families and kids in Winthrop, MA?

The best B&B for families and kids in Winthrop, MA is Beautiful Victorian .

What amenities are commonly offered in bed and breakfasts in Winthrop, MA?

Most bed and breakfasts in Winthrop offer a range of amenities, including complimentary breakfast, free Wi-Fi, and private bathrooms. Some may also offer additional features like fireplaces, outdoor seating, and parking.

What are the best pet friendly bed and breakfasts in Winthrop, MA?

The best pet friendly B&Bs in Winthrop, MA are Solo Traveler Private Bedroom In Winthrop , (S202) Studio Close To Airport - Hospitals & Beach and Private Room Oceanfront .

What are the best bed and breakfasts with parking in Winthrop, MA?

Boston Airport Subway - We're A Licensed 5* Airbnb , Shirley's Sea Breeze Airport Getaway 2 Single Beds and The House On Myrtle are the best B&Bs with parking in Winthrop, MA.

Winthrop, MA Bed and Breakfasts at the Best Price

8.3 7 reviews

Winthrop, MA

22/09 – 23/09

£114/nightfor 1 night

Homestay In Dorchester Near Fields Corner Station

1 2

B&B , Boston

This B&B is situated in Boston's Dorchester district, offering easy access to Fields Corner Station and lying 5.47 kilometres from the JFK Presidential Library & Museum and 6.28 kilometres from the Museum of Fine Arts.
This air-conditioned accommodation, covering 14 square metres with one bedroom and one bathroom, can host up to two guests and provides complimentary WiFi.

8.4 16 reviews

Winthrop, MA

18/10 – 24/10

£92/nighttotal: £552 (6 )

Homestay Near Near Savin Hill Area

1 1

B&B , Boston

This guest house in Boston's Dorchester district is situated 1.6 kilometres from the University of Massachusetts Boston and within 5 kilometres of the Boston Convention and Exhibition Centre and Copley Square, with Savin Hill underground station a 9-minute walk away.
Guests at this B&B can expect complimentary breakfast, free Wi-Fi in common areas, and an on-site laundry facility, with kitchenettes featuring a fridge and microwave oven available.

8.4 48 reviews

Winthrop, MA

19/08 – 28/08

£104/nighttotal: £936 (9 )

Homestay In Fields Corner Area Boston

1 2

B&B , Boston

This Dorchester guest house is situated within 5 kilometres of the Franklin Park Zoo, the University of Massachusetts Boston, and the John F. Kennedy Presidential Library and Museum, with Fields Corner underground station a 7-minute walk away.
Guests at this B&B can expect complimentary breakfast, free Wi-Fi in common areas, on-site laundry facilities, and shared bathrooms, with a fridge and microwave oven available in the kitchen.

Winthrop, MA

22/09 – 23/09

£117/nightfor 1 night

Homestay Near Downtown Boston

1 2

B&B , Boston

This Boston bed and breakfast is situated approximately 4 kilometres from the city centre, offering convenient access to local attractions such as Our Lady of Czestochowa Roman Catholic Church, Carson Beach, and the historic Shirley-Eustis House.
Guests can benefit from complimentary Wi-Fi and a late check-in option between 11:00 PM and 2:00 AM, though a USD 25 fee may apply, with a standard check-out time of 10:00 AM.

9.8 238 reviews

Winthrop, MA

22/09 – 23/09

£298/nightfor 1 night

Steps From Fenway Park + Free Breakfast & Pool

1 2

B&B , Boston

This Boston guesthouse is located in Kenmore Square, a short walk from Fenway Park and the House of Blues.
Offering a retro-rock theme, a heated outdoor pool, complimentary breakfast, and valet parking, this one-bedroom, one-bathroom guesthouse sleeps two and features on-site access to Hojoko Japanese tavern.

9.0 54 reviews

Winthrop, MA

22/09 – 23/09

£110/nightfor 1 night

Homestay In Harvest Street

1 2

B&B , Boston

This Boston homestay, near Andrew Station, offers convenient access to public transport and is a 2.4km walk from Carson Beach, with major attractions such as the John F. Kennedy Presidential Library and Museum within a 2.9km radius.
The 6 square metre self-catering apartment features one bedroom, one bathroom, sleeps five guests, and includes air conditioning, parking, towels, and bed linen.

8.4 69 reviews

Winthrop, MA

22/09 – 23/09

£155/nightfor 1 night

Homestay In Boston West Bellflower Street

1 2

B&B , Boston

This newly constructed B&B in Boston is conveniently located near South Bay Mall and Andrew Train Station, offering easy access to Carson Beach (1.5 km) and the JFK Presidential Library and Museum (3.1 km).
This 14 square metre guest house accommodates up to three people and features a kitchenette with a fridge and microwave, air conditioning, a private balcony, and complimentary Wi-Fi.

7.5 2 reviews

Winthrop, MA

22/09 – 23/09

£115/nightfor 1 night

Airport Room 1

1 2

B&B , Boston

This Boston bed and breakfast is located near Logan Airport, a 12-minute walk from Constitution Beach, and within 6.8 kilometres of downtown attractions such as Boston North Station and TD Garden.
This 150 square metre guesthouse offers 1 bedroom, 1 bathroom, and accommodation for 2 guests, featuring air conditioning, heating, free Wi-Fi, free private parking, and an in-room kitchen with a fridge and kettle.

9.2 131 reviews

Winthrop, MA

19/08 – 28/08

£94/nighttotal: £846 (9 )

Pet-friendly 1-bedroom: Private Entry, Parking, Ac

1 2

B&B , Melrose

This Melrose garden flat offers convenient access to public transport, being within walking distance of MBTA buses and the Oak Grove station on the Orange Line, providing easy access to Boston.
Sleeping up to three guests, this self-contained unit features a private kitchenette with microwave and fridge, a private bathroom, a shared laundry, off-street parking, Wi-Fi, and a private garden-level entrance.

10 38 reviews

Winthrop, MA

18/10 – 24/10

£269/nighttotal: £1614 (6 )

Across Fenway Park + Free Breakfast. Pool. Dining.

1 1

B&B , Boston

The Verb Hotel, a guesthouse in Boston's Kenmore Square, is located steps from Fenway Park and a short walk (approximately 0.8 km) from the House of Blues.
This rock 'n' roll-themed lodging boasts a heated outdoor pool, on-site Japanese tavern (Hojoko), complimentary breakfast, and sleeps four guests in one bedroom with one bathroom, offering a record player and curated vinyl selection.

9.7 853 reviews

Winthrop, MA

22/09 – 23/09

£286/nightfor 1 night

Second Oldest Home In Beacon Hill

1 2

B&B , Boston

This studio apartment is situated on Beacon Hill, a short walk from the Massachusetts State House and Boston Common, offering a peaceful escape in a historic neighbourhood. The property has consistently received excellent ratings for its cleanliness, location, and guest experience.
The studio comfortably accommodates three guests and features a queen-size bed, a well-equipped kitchenette, and a private washer and dryer. Guests can enjoy amenities such as a TV with Roku, a work/dinner table, and personalised touches like coffee, to-go cups, and plates.

Winthrop, MA

22/09 – 23/09

£131/nightfor 1 night

Homestay In Fields Corner Area Boston

1 2

B&B , Boston

This Boston bed and breakfast is situated in the Fields Corner Area, offering a local neighbourhood experience 6 kilometres from the city centre, with Adams/King Playground, Dr. Martin Luther King, Jr. Archives, and Prince Hall Masonic Temple nearby.
Guests can enjoy complimentary Wi-Fi, on-site laundry services, and pet-friendly accommodation at this guesthouse.

Best Winthrop, MA bed and breakfasts with air conditioning

9.7 55 reviews

Winthrop, MA

19/08 – 28/08

£145/nighttotal: £1305 (9 )

Daybed With Trundle - Access To Home Library & Bar

1 2

B&B , Revere

This charming bed and breakfast is situated just a short distance from Revere Beach and the Freedom Trail, offering easy access to the area's top attractions. The property consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The guesthouse features comfortable, well-appointed rooms, each with a private bathroom and modern amenities. Guests can enjoy a range of facilities, including a shared lounge, a fully equipped kitchen, a spa, a bar, a fitness centre, a garden, a terrace, and free parking.

8.6 330 reviews

Winthrop, MA

22/09 – 23/09

£120/nightfor 1 night

Beautiful Victorian House, Room

1 2

B&B , Boston

This charming guest house is located in a quiet residential area of Boston, just 4 kilometres from the JFK Presidential Library & Museum and 7 kilometres from the Boston Museum of Fine Arts. The property consistently receives very good ratings for its cleanliness, location, and overall experience.
The guest house is a Victorian property with a single bedroom and a total floor area of 22 square metres, comfortably accommodating two guests. Amenities include air conditioning, free Wi-Fi, a kitchen, and a terrace, allowing guests to relax and enjoy the peaceful surroundings.

9.9 175 reviews

Winthrop, MA

18/10 – 24/10

£232/nighttotal: £1392 (6 )

Modern Suite Near Boston, Airport & Downtown

1 1

B&B , Chelsea

This Chelsea, Massachusetts private suite, located in the Admiral's Hill neighbourhood, offers easy access to Logan Airport and Boston city centre, being just a short distance from Mary O'Malley Park.
The self-contained apartment features a queen-sized bed, a pull-out sofa bed accommodating up to four guests, a kitchenette with a SMEG coffee maker and full-sized refrigerator, a private bathroom with a shower, and a 55" Samsung Frame Smart TV; off-street parking is also provided within a secure, gated community.

9.0 736 reviews

Winthrop, MA

22/09 – 23/09

£444/nightfor 1 night

Boston Lodge And Suites

2 2

B&B , Boston

Boston Lodge and Suites is located in a quiet suburban area, just a short distance from the JFK Presidential Library & Museum and the Boston Convention Exhibitors Center. The hotel has consistently received very good user ratings, with excellent marks for location and cleanliness.
The accommodation offers a range of rooms and suites, some with dining and seating areas. Guests can enjoy a variety of amenities, including a swimming pool, tennis court, and restaurant, as well as a garden and terrace.

Best Winthrop, MA bed and breakfasts with breakfast included

8.4 283 reviews

Winthrop, MA

22/09 – 23/09

£92/nightfor 1 night

Homestay In Boston Fields Corner Area - 30 Days M

1 2

B&B , Boston

This Boston guesthouse is located in Dorchester's Fields Corner, approximately 6-8km from attractions such as the Museum of Fine Arts, South Station, and the Hynes Convention Centre.
The one-bedroom property, boasting two bathrooms and free Wi-Fi, offers air-conditioned rooms with flat-screen TVs and is conveniently close to the JFK Presidential Library & Museum (5.8km).

9.2 20 reviews

Winthrop, MA

19/08 – 28/08

£84/nighttotal: £756 (9 )

Homestay Near Downtown Boston

1 2

B&B , Boston

This Dorchester guesthouse offers convenient access to the University of Massachusetts Boston, located just 1.1 kilometres away, and is within 5 kilometres of the Boston Convention and Exhibition Centre, Copley Square, Boston Common, and Fenway Park, with Newmarket and Andrew Stations a 10-minute walk providing further transport links. Guests can expect complimentary breakfast, a fridge and microwave oven in the kitchen, and free internet access, though shared bathrooms are provided at this very good rated B&B.

9.4 1120 reviews

Winthrop, MA

18/10 – 24/10

£212/nighttotal: £1272 (6 )

The College Club Of Boston

1 1

B&B , Boston

The College Club of Boston, a three-star hotel, is ideally located in the Back Bay district, a short walk from Boston Public Garden and Boston Common, and approximately 2.1km from Symphony Hall.
This 800 sq ft establishment offers 12 guest rooms, complimentary continental breakfast, free Wi-Fi, on-site meeting space, and a quiet library; pets are welcome.

8.4 44 reviews

Winthrop, MA

18/10 – 24/10

£124/nighttotal: £744 (6 )

Homestay In Boston -

1 1

B&B , Boston

This Dorchester guesthouse offers a local Boston experience, situated 1.2 kilometres from the University of Massachusetts Boston and within 5 kilometres of the Boston Convention and Exhibition Centre, Copley Square, Boston Common, and Fenway Park, with Andrew Station a 9-minute walk away.
Guests can enjoy complimentary breakfast and free WiFi in public areas, with air conditioning and a kitchen equipped with a fridge and microwave oven available.

Frequently asked questions about bed and breakfast in Winthrop, MA

What is the typical weather in Winthrop, MA, and how does it affect outdoor plans?
Winthrop has a typical New England climate with four distinct seasons. Summers are warm and humid, with temperatures averaging around 25°C. Winters are cold and snowy, with temperatures often below freezing. Plan outdoor activities accordingly, as some attractions may be closed during the winter months.
What are the best bed and breakfasts in Winthrop, MA?
Among the B&Bs in Winthrop, MA, Boston Airport Subway - We're A Licensed 5* Airbnb, Shirley's Sea Breeze Airport Getaway 2 Single Beds and House By The Beach - Boston - Airport are the most popular ones.
What are the best cultural activities and events in and around Winthrop, MA?
Winthrop hosts a number of cultural events throughout the year, including the annual Winthrop Summerfest in July, which features live music, food vendors, and family-friendly activities. The town also has a vibrant arts scene, with several local galleries and studios.
What are the best bed and breakfasts with a pool in Winthrop, MA?
One Bedroom Suite In Boutique Inn, Heaven Room and Oasis Room are the best B&Bs with a pool in Winthrop, MA.
Which hiking trails are recommended for exploring in and around Winthrop, MA?
While Winthrop itself doesn't have many dedicated hiking trails, you can find some great options nearby. The 'Belle Isle Marsh Reservation' in East Boston offers a variety of trails along the waterfront, and the 'Lynn Woods Reservation' in Lynn has over 1200 acres of trails for hiking, biking, and horseback riding.
What are the best bed and breakfasts for families and kids in Winthrop, MA?
The best B&B for families and kids in Winthrop, MA is Beautiful Victorian.
What amenities are commonly offered in bed and breakfasts in Winthrop, MA?
Most bed and breakfasts in Winthrop offer a range of amenities, including complimentary breakfast, free Wi-Fi, and private bathrooms. Some may also offer additional features like fireplaces, outdoor seating, and parking.
What are the best pet friendly bed and breakfasts in Winthrop, MA?
The best pet friendly B&Bs in Winthrop, MA are Solo Traveler Private Bedroom In Winthrop, (S202) Studio Close To Airport - Hospitals & Beach and Private Room Oceanfront.
What are the best bed and breakfasts with parking in Winthrop, MA?
Boston Airport Subway - We're A Licensed 5* Airbnb, Shirley's Sea Breeze Airport Getaway 2 Single Beds and The House On Myrtle are the best B&Bs with parking in Winthrop, MA.

Destinations nearby

Best Winthrop, MA bed and breakfasts with a garden

9.2 271 reviews

Winthrop, MA

18/10 – 24/10

£575/nighttotal: £3450 (6 )

Clarendon Square

1 1

B&B , Boston

Clarendon Square is a charming bed and breakfast situated in Boston's Back Bay neighbourhood, just a short walk from the Back Bay station and within easy reach of the city centre. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This comfortable guesthouse is ideal for couples, offering a single bedroom and bathroom. Guests can enjoy a range of amenities, including a hot tub, a sun terrace, a tennis court, and a garden, as well as free Wi-Fi and room service.

8.7 701 reviews

Winthrop, MA

22/09 – 23/09

£148/nightfor 1 night

Boston Monadnock Properties

1 2

B&B , Boston

Boston Monadnock Properties is located in a peaceful residential area, just a short distance from Carson Beach and within easy reach of several Boston landmarks. The guesthouse has received very good user ratings and is praised for its excellent cleanliness and good location.
Each room at this guesthouse features a kitchenette with an oven, microwave, toaster, and fridge, allowing guests to prepare their own meals. Guests can also enjoy a garden, a shared lounge, free Wi-Fi, and air conditioning.

Top Bed and Breakfasts with a Pool in Winthrop, MA

A B&B in Winthrop, MA with a swimming pool ensures a refreshing dip to complement your adventures is always an option.

9.8 240 reviews

Winthrop, MA

18/10 – 24/10

£253/nighttotal: £1518 (6 )

Walk To Fenway Park With Free Breakfast & Pool

1 1

B&B , Boston

This Boston guesthouse, The Verb Hotel, is located in Kenmore Square, a short walk from Fenway Park and the House of Blues.
Offering one bedroom sleeping up to four guests, it features a retro-rock theme, a heated outdoor pool, on-site Japanese tavern (Hojoko), complimentary breakfast, and valet parking (fees apply); dog-friendly rooms are also available.

9.7 558 reviews

Winthrop, MA

22/09 – 23/09

£194/nightfor 1 night

Queen-sdb Privée Avec Douche-vue Sur Port-blue Wat

1 2

B&B , Boston

This unique B&B is situated at Constitution Marina in Boston Harbour, a short walk from the Boston Tea Party Ships & Museum and a short drive from the Freedom Trail. The B&B has received excellent ratings for location, cleanliness, and overall experience.
The B&B is a spacious sailboat with a comfortable deck and seating area. It offers modern amenities such as air conditioning, heating, cable TV, Wi-Fi, and a refrigerator, as well as a delicious breakfast included in the price.

Top-Rated Coastal Bed and Breakfasts in Winthrop, MA

Take in the relaxing maritime atmosphere at shoreside bed and breakfasts a short distance from the coast in Winthrop, MA.

9.4 15 reviews

Winthrop, MA

19/08 – 28/08

£145/nighttotal: £1305 (9 )

Iii New Apartment With Luxury Amenities In Boston#3727375

1 2

B&B , Boston

Choose the Right Luxury Bed and Breakfasts in Winthrop, MA

Exquisite comfort and a prime location define these luxury B&Bs in Winthrop, MA, offering a premium experience from the moment you arrive.

8.3 7 reviews

Winthrop, MA

22/09 – 23/09

£114/nightfor 1 night

Homestay In Dorchester Near Fields Corner Station

1 2

B&B , Boston

Popular Bed and Breakfasts with Parking in Winthrop, MA

Free on-site parking comes with these B&Bs in Winthrop, MA, letting you focus entirely on the local beaches from the start.

8.5 31 reviews

Winthrop, MA

22/09 – 23/09

£132/nightfor 1 night

Homestay In Boston Pearl Street

1 2

B&B , Boston

8.1 12 reviews

Winthrop, MA

22/09 – 23/09

£149/nightfor 1 night

Ocean Spray Inn

1 2

B&B , Winthrop Town

Browse Bed and Breakfasts with a Hot Tub in Winthrop, MA

Returning to a hot tub after a day of discovery transforms your stay; these B&Bs in Winthrop, MA each feature one for your enjoyment.

8.7 701 reviews

Winthrop, MA

22/09 – 23/09

£148/nightfor 1 night

Boston Monadnock Properties

1 2

B&B , Boston

Discover Bed and Breakfasts with a Spa in Winthrop, MA

Choose a spa-equipped B&B in Winthrop, MA for the ultimate waterside wellness experience integrated seamlessly into your relaxing stay.

8.3 7 reviews

Winthrop, MA

22/09 – 23/09

£114/nightfor 1 night

Homestay In Dorchester Near Fields Corner Station

1 2

B&B , Boston

Bed and Breakfast in Winthrop, MA

12 Bed and Breakfasts and Inn in Winthrop, MA

Homestay In Dorchester Near Fields Corner Station

Homestay Near Near Savin Hill Area

Homestay In Fields Corner Area Boston

Homestay Near Downtown Boston

Steps From Fenway Park + Free Breakfast & Pool

Homestay In Harvest Street

Homestay In Boston West Bellflower Street

Airport Room 1

Pet-friendly 1-bedroom: Private Entry, Parking, Ac

Across Fenway Park + Free Breakfast. Pool. Dining.

Second Oldest Home In Beacon Hill

Homestay In Fields Corner Area Boston

Daybed With Trundle - Access To Home Library & Bar

Beautiful Victorian House, Room

Modern Suite Near Boston, Airport & Downtown

Boston Lodge And Suites

Homestay In Boston Fields Corner Area - 30 Days M

Homestay Near Downtown Boston

The College Club Of Boston

Homestay In Boston -

Clarendon Square

Boston Monadnock Properties

Walk To Fenway Park With Free Breakfast & Pool

Queen-sdb Privée Avec Douche-vue Sur Port-blue Wat

Iii New Apartment With Luxury Amenities In Boston#3727375

Homestay In Dorchester Near Fields Corner Station

Homestay In Boston Pearl Street

Ocean Spray Inn

Boston Monadnock Properties

Homestay In Dorchester Near Fields Corner Station