Compare Vacation Rentals & Airbnb in Winthrop, MA

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Winthrop, MA vacation rentals
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254 Rentals and Airbnb in Winthrop, MA

Best family friendly Winthrop, MA vacation rentals

Among the 254 accommodations in Winthrop, MA, here are the 4 best family friendly rentals

Pet-friendly Malden Apartment: 7 Mi To Boston! - Winthrop, MA
No reviews

Pet-friendly Malden Apartment: 7 Mi To Boston!

apartment, Malden
This Malden apartment, near Malden Centre station, is conveniently located 3.9km from Encore Boston Harbor and within 9.7km of Boston's TD Garden and Harvard University.
The 93 square metre flat offers two bedrooms, one bathroom, sleeps three, and includes a fully equipped kitchen, in-unit laundry, parking, and internet access.
Brand New Luxury Retreat W/ Pool & Fitness Center - Winthrop, MA
9.8 8 reviews

Brand New Luxury Retreat W/ Pool & Fitness Center

apartment, Boston
This 2-bedroom flat is located in South Boston, a short distance from Carson Beach and Downtown Boston, with convenient access to the Red Line for travel across the city.
This accommodation offers a fully equipped kitchen with stainless steel appliances, air conditioning, a swimming pool, a fitness centre, and secure garage parking, suitable for up to five guests.
Lux 2br W Gym Pool Sleep 6 In Assembly Square - Winthrop, MA
No reviews

Lux 2br W Gym Pool Sleep 6 In Assembly Square

apartment, Somerville
This two-bedroom flat is situated in Somerville's waterfront Assembly Square district, a mere 5-minute walk from Assembly Row and LEGOLAND® Discovery Centre, with the Assembly subway station providing convenient access for exploring Boston.
This 111 square metre residence accommodates up to six guests and features a fully equipped kitchen, air conditioning, Wi-Fi, and on-site covered parking, alongside a terrace/patio and barbecue area for outdoor enjoyment.
62 M² Apartment ∙ 1 Bedroom ∙ 3 Guests - Winthrop, MA
No reviews

62 M² Apartment ∙ 1 Bedroom ∙ 3 Guests

apartment, Boston
This Boston flat is located in the Seaport district, within 1.2 kilometers of the Children's Museum, Boston Tea Party Museum, and New England Aquarium, and offers direct access to Logan International Airport via the Silver Line.
This 62 square meter flat, suitable for up to three guests, features two bedrooms, one bathroom, a fully equipped kitchen, and access to an on-site fitness centre and over 836 square meters of outdoor space.

Best Winthrop, MA vacation rentals with a pool

Among the 254 accommodations in Winthrop, MA, here are the 4 best rentals with a pool

Luxury 2br Cambridge | Pool + Parking - Winthrop, MA
No reviews

Luxury 2br Cambridge | Pool + Parking

apartment, Cambridge
This 2-bedroom flat in East Cambridge offers proximity to Harvard University and MIT, with the Charles River just 400 metres away and cultural sites such as the Berklee College of Music and the Boston Museum of Fine Arts within easy reach.
This modern accommodation, suitable for up to 5 guests, includes parking and air conditioning, with convenient access to Faneuil Hall Marketplace, Fenway Park, and TD Garden for entertainment and sporting events.
2-bedroom Apart In Cambridge With Balcony Garage Parking - Winthrop, MA
10 1 review

2-bedroom Apart In Cambridge With Balcony Garage Parking

apartment, Boston
This Cambridge flat offers excellent access to Boston's renowned academic institutions and cultural attractions, with its precise location within Cambridge providing convenient access to the city's academic and cultural hubs.
This two-bedroom flat accommodates up to four guests and features two bathrooms, a microwave, dishwasher, air conditioning, and an on-site fitness room, ensuring a comfortable and convenient stay.
Curated Designer Retreat  Pool  Gym  Dining - Winthrop, MA
10 28 reviews

Curated Designer Retreat Pool Gym Dining

apartment, Everett
This Everett flat is centrally located, offering convenient access to Encore Boston Harbor (approximately 640 metres) and LEGOLAND Discovery Center (approximately 960 metres).
This 92 square metre residence accommodates up to 5 guests with 6 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a swimming pool, garden, spa, and covered parking, with an 11:00 check-out time.
Central 1br Apartment Assembly Square Pool Gym Parking Sleep 5 - Winthrop, MA
No reviews

Central 1br Apartment Assembly Square Pool Gym Parking Sleep 5

apartment, Somerville
This Somerville flat is situated in the Winter Hill district, offering a 1.4 kilometre walk to Cambridge College and is 4 kilometres from Inman Square and Boston's North Station and TD Garden.
This 65 square metre apartment accommodates up to seven guests and features a kitchen with a fridge, microwave and dishwasher, air conditioning, a swimming pool, garden, fitness centre, and complimentary on-site parking with free Wi-Fi.

Frequently Asked Questions about vacation rentals in Winthrop, MA

  • Which neighborhood in Winthrop, MA should you consider for a vacation rental?

    The area around Winthrop Beach is a popular choice. There are plenty of vacation rentals available, and you'll be close to the beach, restaurants, and shops.
  • What are the best Airbnb and vacation rentals in Winthrop, MA?

  • What are the top family-friendly attractions in Winthrop, MA?

    The Winthrop Town Beach is a great option for families, with a playground, picnic areas, and plenty of space to run around. The Winthrop Public Library also has a children's section with story time and other activities.
  • What are the most popular Airbnbs in Winthrop, MA?

  • When is the best time to book a vacation rental in Winthrop, MA?

    The best time to book a vacation rental in Winthrop is during the summer months, from June to August, when the weather is warm and sunny. However, if you're looking for a quieter experience, you can book a rental in the spring or autumn.
  • What are the best vacation rentals with a pool in Winthrop, MA?

  • What are the best budget-friendly activities in Winthrop, MA?

    A walk along the Winthrop Shore Reservation is a great way to enjoy the scenery without spending any money. You can also visit the Winthrop Public Library for free events and activities.
  • What are the best rentals for families and kids in Winthrop, MA?

  • What are the best restaurants with local dishes in Winthrop, MA?

    The Winthrop Fish Market is a great option for fresh seafood. You can also try the classic New England clam chowder at the Beachcomber Restaurant.
  • What are the best rentals or Airbnbs with a jacuzzi in Winthrop, MA?

    Boardwalk To Beach - Coastal Ne Town and Boston Sandy Shanty: Single Home Steps To The Sea are the best vacation rentals or Airbnb with a jacuzzi in Winthrop, MA.

  • What are the best walking or cycling routes in Winthrop, MA?

    The Winthrop Shore Reservation offers a scenic walking and cycling route along the coast. You can also bike along the Winthrop Parkway, which offers views of the Boston skyline.
  • Are there pet-friendly attractions in Winthrop, MA?

    The Winthrop Town Beach is pet-friendly during certain hours of the day. You can also walk your dog along the Winthrop Shore Reservation.
  • What are the benefits of choosing a vacation rental in Winthrop, MA?

    Vacation rentals offer more space and privacy than a hotel room. You'll also have access to a kitchen, which can save you money on dining out. Some rentals also have amenities like a pool or hot tub.
  • What are the top sports attractions and facilities in Winthrop, MA?

    Winthrop has a few sports facilities, including the Winthrop Golf Course and the Winthrop Recreation Center. The Winthrop High School also has a sports field and a gymnasium.

Popular destinations

Best Winthrop, MA vacation rentals with a balcony

Best Location In Boston - Winthrop, MA
10 1 review

Best Location In Boston

apartment, Boston
This South Boston flat offers excellent proximity to Logan Airport, Downtown Boston, and the beach, all within a 5-minute drive, and is a short walk from Faneuil Hall Marketplace and the Freedom Trail.
This family-friendly residence accommodates up to six guests in three bedrooms, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, two balconies, and private parking.
Luxury 1br Next To Broadway Southie Dpcu - Winthrop, MA
9.8 10 reviews

Luxury 1br Next To Broadway Southie Dpcu

apartment, Boston
This luxury one-bedroom flat is situated at the start of South Boston, a mere 200 metres from the Broadway Red Line station, providing swift access to central Boston attractions and Massachusetts General Hospital.
This 71 square metre flat offers a fully equipped kitchen, a King bed and sofa bed for two guests, and building amenities include a rooftop terrace with city views, all within easy reach of restaurants, entertainment, and Boston Common.
Modern 3br Pet-friendly Boston Apt W/parking  Fenway Park & Td Garden 30/3 - Winthrop, MA
9.2 26 reviews

Modern 3br Pet-friendly Boston Apt W/parking Fenway Park & Td Garden 30/3

apartment, Boston
This Dorchester apartment, situated near Savin Hill and Fields Corner stations, offers easy access to the University of Massachusetts Boston (2.3 km) and Franklin Park Zoo (4.8 km).
This three-bedroom, two-bathroom property sleeps up to ten guests and boasts free parking, Wi-Fi, a balcony, and a garden, making it ideal for families or groups visiting Boston.
Luxury Studio Next To Broadway 8svt - Winthrop, MA
10 1 review

Luxury Studio Next To Broadway 8svt

studio, Boston
This South Boston apartment is ideally located a 2-minute walk from the Broadway station on the Red Line, offering easy access to Boston Common, Emerson College, and the Seaport District, all within a 3.2km radius.
The 42-square-metre studio flat sleeps two guests and boasts a fully equipped kitchen, in-unit laundry, a terrace, and access to a rooftop offering city views; nearby amenities include restaurants, shops, and the Massachusetts General Hospital (MGH) a short subway ride away.

Best Winthrop, MA vacation rentals with parking

Smart Tv Pool Full Kitchen 20min Airport King - Winthrop, MA
9.4 29 reviews

Smart Tv Pool Full Kitchen 20min Airport King

resort, Malden
This professionally managed luxury apartment complex in Malden offers a central location with excellent access to local amenities and landmarks.
The "Smart Tv Pool Full Kitchen 20min Airport King" offer includes one bedroom, one bathroom, and accommodates up to four guests, featuring air conditioning, internet, a swimming pool, garden, fitness centre, and parking, with pets and families welcome.
Boston Views 2 Without The Expense - Winthrop, MA
8.8 86 reviews

Boston Views 2 Without The Expense

apartment, Everett
This Everett apartment, a short distance from Boston, offers easy access to public transport, including buses and Wellington station, and is conveniently located near the Tobin Bridge.
The two-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen with Boston skyline views from its porch, and includes off-street parking.
Sterling 1br At Everett | Pool & Gym - Winthrop, MA
9.8 50 reviews

Sterling 1br At Everett | Pool & Gym

apartment, Everett
This Everett flat offers contemporary comfort, located just minutes from the Encore Boston Harbour and Assembly Row, with excellent access to major highways for travel throughout Greater Boston.
This one-bedroom apartment sleeps up to four guests and features air conditioning, in-unit laundry, a fully equipped kitchen with stainless steel appliances, and access to communal amenities including a swimming pool, fitness centre, and BBQ stations.
Peaceful 2br Near Us Route 1 And Boston - Winthrop, MA
9.5 6 reviews

Peaceful 2br Near Us Route 1 And Boston

apartment, Melrose
This Melrose flat provides easy access to Boston, situated 11.5 kilometres from Boston North Station and TD Garden, and 9.1 kilometres from Cambridge College.
This one-bedroom dwelling, covering 14 square metres and accommodating up to seven guests, features a kitchen with a fridge, microwave, and dishwasher, air conditioning, free Wi-Fi, and private parking, alongside an outdoor dining area.
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