Best apartment offers in Winthrop, MA

252 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Winthrop, MA apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

252 Best apartments in Winthrop, MA

Best family friendly Winthrop, MA Holiday Apartments and Self Catering Accommodations

Among the 252 accommodations in Winthrop, MA, here are the 4 best family friendly holiday apartments

Chic 3br1.5ba City Stay - Near T + Parking - Winthrop, MA
No reviews

Chic 3br1.5ba City Stay - Near T + Parking

apartment, Boston
This 3-bedroom flat in Boston's Dorchester district is a convenient 7-10 minute walk from the Savin Hill T station, providing easy access to the city's attractions.
This family-friendly accommodation offers off-street parking, air conditioning, a kitchen with essential appliances, and a terrace, comfortably sleeping up to 11 guests with its adaptable futon sofas.
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.
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.
Luxurious 2br - 2ba Apt At Hyatus - Winthrop, MA
9.4 30 reviews

Luxurious 2br - 2ba Apt At Hyatus

apartment, Somerville
This Somerville apartment, ideally located near Davis Square, Union Square, and Assembly Row, offers easy access to the Orange Line and is within walking distance of numerous shops and restaurants.
The 93 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes amenities such as a swimming pool, spa, and secure parking; the building also features a fitness centre and co-working spaces.

Best Holiday Apartments and Self Catering Accommodations in Winthrop, MA with a pool

Among the 252 accommodations in Winthrop, MA, here are the 4 best apartments with a pool

Elegant 2br - 2ba Oasis With Pool & Gym - Winthrop, MA
10 7 reviews

Elegant 2br - 2ba Oasis With Pool & Gym

apartment, Everett
This centrally located Everett apartment offers easy access to Encore Boston Harbor (a 4-minute drive) and Assembly Row (a 6-minute drive), and is a 14-minute walk from Chelsea station.
The 93-square-metre (1000 sq ft) property boasts six bedrooms, two bathrooms, accommodates six guests, and includes amenities such as a swimming pool, garden, and a fully equipped kitchen.
Entire One Bedroom Apartment - Winthrop, MA
9.8 9 reviews

Entire One Bedroom Apartment

apartment, Chelsea
This one-bedroom flat is located in the heart of Chelsea, just a short walk from the Chelsea Market and the High Line, offering easy access to the area's attractions and a peaceful atmosphere.
The flat is ideal for a solo traveller or a couple, providing a comfortable bedroom, a fully equipped kitchen and a bathroom. It also features a range of amenities including air conditioning, a swimming pool, a garden, a fitness centre and parking.
Luxe Everett 2br2ba W/ Pool, Gym & Parking - Winthrop, MA
9.0 7 reviews

Luxe Everett 2br2ba W/ Pool, Gym & Parking

apartment, Everett
This Everett flat is centrally located, a 5-minute drive from TD Garden and a 7-minute drive from the New England Aquarium, with Chelsea Station a 14-minute walk away.
This 84 square metre property offers 6 bedrooms, 2 bathrooms, and accommodates up to 5 guests, featuring air conditioning, a fully equipped kitchen, a communal pool, a garden, and on-site barbecue and billiards facilities.
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.

Frequently asked questions about apartment rentals in Winthrop, MA

  • What makes Winthrop, MA unique or famous?

    Winthrop is known for its beautiful beaches, especially the long stretch of sand at Winthrop Beach. It's also a popular spot for fishing and boating, with a vibrant maritime culture. The town's proximity to Boston makes it an attractive option for those looking for a quieter, more relaxed lifestyle while still being close to the city.
  • Where can you find the best local markets and street food in Winthrop, MA?

    Winthrop doesn't really have a bustling street food scene, but you can find local produce and fresh seafood at the Winthrop Farmers Market, which takes place on Saturdays during the summer months. For a more casual dining experience, there are a few local restaurants and cafes in the town centre.
  • What leisure activities are available for relaxation in Winthrop, MA?

    Winthrop offers a variety of options for relaxation, from strolling along the beach to exploring the scenic trails at the Winthrop Shore Reservation. You can also enjoy a round of golf at the Winthrop Golf Course or simply relax with a book at the Winthrop Public Library.

Popular destinations

Best Winthrop, MA holiday apartments with air conditioning

Big, Cozy Home  Walk To T, Free Parking, Yard - Winthrop, MA
10 6 reviews

Big, Cozy Home Walk To T, Free Parking, Yard

apartment, Boston
This stylish three-bedroom apartment in Boston's Orient Heights neighbourhood is a 9-minute walk (approximately 0.8 km) from Suffolk Downs T station, offering easy access to downtown Boston, Logan International Airport, and other key areas.
The property, sleeping up to seven guests, boasts a private fenced yard, in-unit laundry (LG washer and dryer), free on-street parking, a fully equipped kitchen including a dishwasher, and a 60" Samsung Smart TV; nearby attractions include beaches, museums, and major hospitals.
Spacious 2br Fidi District Centrally Located - Winthrop, MA
9.0 1 review

Spacious 2br Fidi District Centrally Located

apartment, Boston
This Boston apartment, situated in the prime Financial District, is a short distance (approximately 1 kilometre) from the Freedom Trail and King's Chapel Burying Ground.
The 100 square metre, two-bedroom, two-bathroom flat sleeps seven, offering a fully equipped kitchen, in-unit laundry, air conditioning, and free Wi-Fi.
Close 2 City Swankymodrn  Unit W Centrl Air - Winthrop, MA
9.7 123 reviews

Close 2 City Swankymodrn Unit W Centrl Air

apartment, Boston
This Savin Hill flat is a short walk from the Red Line T station, offering easy access to Boston city centre and is approximately 1.6 km from the Seaport district and Haymarket.
The two-bedroom, one-bathroom apartment sleeps three, features a private rear porch, central air conditioning, hardwood floors and is conveniently located near Savin Hill's beach and playground.
South End Escape Your Family's Dream Getaway - Winthrop, MA
No reviews

South End Escape Your Family's Dream Getaway

apartment, Boston
This South End flat is a 16-minute walk from Boston South Station and 1.1 kilometres from Back Bay, placing you close to attractions such as the Freedom Trail and Boston Common.
This 111 square metre residence offers three bedrooms, two bathrooms, a fireplace, and a water park, with on-site amenities including a fitness centre and swimming pool, and allows pets.

Best pet-friendly Winthrop, MA holiday apartments

Among the 252 accommodations in Winthrop, MA, here are the 4 best pet friendly holiday apartments

#9 Studio Apartment At A Marina - Winthrop, MA
9.2 13 reviews

#9 Studio Apartment At A Marina

apartment, Chelsea
This Chelsea flat boasts excellent transport links, being 0.8 km from the nearest MBTA bus stop and 0.5 km from Market Basket supermarket.
The modern, pet-friendly apartment sleeps two, features a full kitchen with high-end appliances, a garden, parking, and water views from a large deck; on-site laundry facilities are also available.
South End Oasis W Pool & Gym - Winthrop, MA
No reviews

South End Oasis W Pool & Gym

apartment, Boston
This South End flat offers excellent access, being a 13-minute walk from Boston South Station and 0.6 kilometres from Back Bay, with landmarks such as the Boston Tea Party Ship & Museum and the Freedom Trail within easy reach.
This 70 square metre residence accommodates up to 7 guests with a separate bedroom and living room, featuring a private patio, fireplace, air conditioning, free WiFi, a fully equipped kitchen, and on-site access to a swimming pool and fitness centre.
Morden King Room In  Boston King (Tropical Vibez#2) - Winthrop, MA
No reviews

Morden King Room In Boston King (Tropical Vibez#2)

apartment, Boston
This 1-bedroom flat is situated in Boston's Roxbury district, offering convenient access to the Museum of Fine Arts and Berklee College of Music, as well as proximity to Boston Harbour and Flynn Cruiseport Boston.
This property accommodates two guests and features air conditioning, Wi-Fi, and a private balcony, with an 11:00 check-out time.
Family-friendly 4br Boston Near T W/parking & Laundry  Easy City Access 233/3 - Winthrop, MA
8.6 42 reviews

Family-friendly 4br Boston Near T W/parking & Laundry Easy City Access 233/3

apartment, Boston
This apartment is situated near Franklin Park Zoo, just a short distance from the Arnold Arboretum and 15 minutes from downtown Boston and Fenway Park, making it a convenient base for exploring the city. It has received excellent ratings for cleanliness and user experience, and a very good rating for location.
The apartment is a spacious four-bedroom property, ideal for accommodating up to 13 guests. It is equipped with a range of amenities, including a fully equipped kitchen, free Wi-Fi, a washer and dryer, and secure parking, ensuring a comfortable and convenient stay.
©2026 cozycozy.com