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Winthrop, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Winthrop, MA

Best Winthrop, MA vacation rentals with a balcony

233-1 4br Boston - Cozy Apt Near Mbta Station - Winthrop, MA
9.4 6 reviews
Winthrop, MA
08/14 – 08/21
$1428/nighttotal: $9996 (7 )

233-1 4br Boston - Cozy Apt Near Mbta Station

4 10
apartment , Boston
This spacious Boston apartment rental is located approximately 3-4 miles from the John F. Kennedy Presidential Library and Museum, Museum of Fine Arts, and South Station.
The 1600-square-foot, four-bedroom unit sleeps up to 27 guests and boasts amenities including a fully equipped kitchen, private parking, a terrace, and concierge service.
233-3 - 4br Boston - Comfortable Family Stay Near Park Zoo - Winthrop, MA
8.2 27 reviews
Winthrop, MA
08/14 – 08/21
$854/nighttotal: $5978 (7 )

233-3 - 4br Boston - Comfortable Family Stay Near Park Zoo

4 10
apartment , Boston
This family-friendly Boston apartment, located approximately 3-4 miles from the JFK Presidential Library and Museum, the Museum of Fine Arts, South Station, and Back Bay, offers convenient access to major attractions.
The 1700-square-foot rental boasts four bedrooms, two bathrooms, sleeps up to 23 guests, and includes amenities such as a fully equipped kitchen, private terrace, free parking, and Wi-Fi.
Luxury Furnished Apartment Near Logan Airport - Winthrop, MA
8.7 32 reviews
Winthrop, MA
08/14 – 08/21
$1292/nighttotal: $9044 (7 )

Luxury Furnished Apartment Near Logan Airport

5 10
apartment , Boston
This East Boston apartment rental is conveniently located approximately 2 miles from Boston's Freedom Trail, North Station, TD Garden, and Old North Church, and 1.3 miles from Constitution Beach, offering easy access to major attractions and Logan Airport (6.8 miles).
The one-bedroom unit features a fully equipped kitchen with dishwasher, air conditioning, a private bathroom, free Wi-Fi, and a terrace/balcony plus access to a garden.
30-1 - 4br Boston - Cozy Apt Near Geneva Cliffs - Winthrop, MA
9.2 10 reviews
Winthrop, MA
08/14 – 08/21
$1166/nighttotal: $8162 (7 )

30-1 - 4br Boston - Cozy Apt Near Geneva Cliffs

4 10
apartment , Boston
This spacious Boston apartment, located near Carson Beach (1.8 miles) and the John F. Kennedy Presidential Library and Museum (2.8 miles), offers easy access to major attractions.
The 1400-square-foot rental boasts four bedrooms, one bathroom, free parking, Wi-Fi, and a fully equipped kitchen, comfortably accommodating up to 18 guests.

Browse Family-Friendly Vacation Rentals in Winthrop, MA

Find the perfect family vacation rental or Airbnb in Winthrop, MA with plenty of room to spread out near local beaches.

5 Bedroom Historic Home Minutes To Boston With Yard - Winthrop, MA
10 12 reviews
Winthrop, MA
08/14 – 08/21
$1097/nighttotal: $7679 (7 )

5 Bedroom Historic Home Minutes To Boston With Yard

5 10
apartment , Medford
This five-bedroom Medford home, located four miles from Boston and a short walk from Station Landing and Assembly Row, offers easy access to public transportation and local attractions.
The 2,000-square-foot rental boasts a private backyard with a gas grill, ample parking, and accommodates up to twelve guests with five queen-sized bedrooms and two bathrooms.
Charming 4r Boston Home W/parking, 5 Min To Casino - Winthrop, MA
9.8 115 reviews
Winthrop, MA
08/14 – 08/21
$558/nighttotal: $3906 (7 )

Charming 4r Boston Home W/parking, 5 Min To Casino

4 10
apartment , Everett
This 4-bedroom apartment is conveniently located in Everett, just a short drive from downtown Boston, Fenway Park, and other popular attractions. The apartment boasts excellent ratings for cleanliness, location, and user experience, ensuring a comfortable and enjoyable stay.
The apartment features a spacious layout with two bathrooms, comfortably accommodating up to 10 guests. Enjoy a well-equipped kitchen, a relaxing patio backyard, and a basement entertainment room for added fun and convenience.
Sage Apartments Boston Logan Airport Chelsea - Winthrop, MA
Winthrop, MA
08/14 – 08/21
$1068/nighttotal: $7476 (7 )

Sage Apartments Boston Logan Airport Chelsea

2 10
apartment , Chelsea
Sage Apartments Boston Logan Airport Chelsea is located in Chelsea, just a short distance from Logan Airport and within easy reach of Boston's Freedom Trail and North Station. This apartment complex boasts excellent user, location, and cleanliness ratings.
Each unit features a fully equipped kitchen, a flat-screen TV, a private bathroom, and comfortable seating. Guests can enjoy amenities like a fitness room, free Wi-Fi, and private parking.
Hyatus Luxury Residences Boston Everett Marquis Collection - Winthrop, MA
9.6 12 reviews
Winthrop, MA
08/14 – 08/21
$1120/nighttotal: $7840 (7 )

Hyatus Luxury Residences Boston Everett Marquis Collection

4 10
apartment , Everett
This 2-bedroom apartment in Everett is located 4.5 miles from Cambridge College and 5.7 miles from North Station and TD Garden.
This 1000 sq ft unit offers air conditioning, complimentary Wi-Fi, a full kitchen, two bathrooms, an outdoor pool, a shared lounge, and an on-site bar with a billiards table, accommodating up to 9 guests.

Frequently Asked Questions about vacation rentals in Winthrop, MA

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

    The Winthrop Beach is a great place to spend a day with the family. There's also a playground at the Winthrop Shore Reservation, and the Winthrop Public Library has a great children's section.
  • What are the best Airbnb and vacation rentals 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. You'll want to book early though, as rentals tend to fill up fast.
  • What are the most popular Airbnbs in Winthrop, MA?

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

    Take a walk along the Winthrop Shore Reservation, it's a great way to get some exercise and enjoy the views. You can also visit the Winthrop Public Library, which has a great selection of books and other resources.
  • What are the best vacation rentals with a pool in Winthrop, MA?

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

    The Winthrop Fish Market is a great place to get fresh seafood. There's also a lot of great Italian food in Winthrop, like the restaurant called The Italian Kitchen.
  • What are the best rentals for families and kids in Winthrop, MA?

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

    The Winthrop Shore Reservation has a great walking and cycling path that runs along the waterfront. You can also take a scenic bike ride through the residential streets of Winthrop.
  • 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.

  • Are there pet-friendly attractions in Winthrop, MA?

    The Winthrop Shore Reservation is pet-friendly, and there are many dog-friendly beaches in the area. You can also find some pet-friendly restaurants in Winthrop.
  • What are the benefits of choosing a vacation rental in Winthrop, MA?

    Vacation rentals in Winthrop offer more space and privacy than hotels. They often come with amenities like a kitchen and laundry facilities, which can be helpful for families or groups. You can also find vacation rentals in a variety of locations, from beachfront properties to homes in quieter neighborhoods.
  • What are the top sports attractions and facilities in Winthrop, MA?

    Winthrop has a few different sports facilities, including the Winthrop High School athletic fields and the Winthrop YMCA. The town also has a few different beaches that are great for swimming, sunbathing, and surfing.

Destinations nearby

Best Winthrop, MA vacation rentals with parking

85a Charming, Cozy 3br, 2ba Home Near Downtown Boston - Winthrop, MA
9.6 7 reviews
Winthrop, MA
08/14 – 08/21
$792/nighttotal: $5544 (7 )

85a Charming, Cozy 3br, 2ba Home Near Downtown Boston

3 10
apartment , Boston
This three-bedroom, two-bathroom Dorchester apartment offers easy access to the Boston subway via Fields Corner and Four Corners/Geneva Ave stations, a short drive from Franklin Park Zoo and the Samuel Adams Brewery.
The 3-bedroom rental sleeps 12 guests and includes free Wi-Fi, a smart TV, a full kitchen with dishwasher, in-unit laundry, air conditioning, on-site parking, and a safe.
Family & Group Haven Near Downtown Retreat - Winthrop, MA
9.1 93 reviews
Winthrop, MA
08/14 – 08/21
$524/nighttotal: $3668 (7 )

Family & Group Haven Near Downtown Retreat

1 10
apartment , Boston
This Boston home is located in the Dorchester district, just a short drive from UMass Boston and Fenway Park, offering easy access to both the city's attractions and its quieter neighborhoods. It boasts excellent user ratings for cleanliness, location, and overall experience.
This 5-bedroom, 2-bathroom house comfortably sleeps 14 guests, making it perfect for families or groups. The house includes a spacious living room, a fully equipped kitchen, a private deck, and a dedicated workspace, along with amenities like air conditioning, parking, and a garden.
Historic And Charming Brownstone - Winthrop, MA
9.8 58 reviews
Winthrop, MA
08/14 – 08/21
$1589/nighttotal: $11123 (7 )

Historic And Charming Brownstone

4 10
apartment , Boston
This Charlestown vacation home is located less than 2 kilometers from the Bunker Hill Monument and within 5 kilometers of the Museum of Science, TD Garden, and Boston Common.
This spacious 2,560-square-foot house features a four-bedroom layout, three bathrooms, sleeps up to ten guests, and includes a private yard, balcony, in-unit laundry, and a fully equipped kitchen.
Chic 3br1.5ba City Stay - Near T + Parking - Winthrop, MA
Winthrop, MA
08/14 – 08/21
$774/nighttotal: $5418 (7 )

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

3 10
apartment , Boston
This 3-bedroom, 2-bathroom rental unit is located on the 3rd floor in Dorchester, Boston, a 7-10 minute walk (approximately 2,100-3,500 feet) from the Savin Hill T station, offering convenient access to Boston attractions.
This family-friendly lodging accommodates up to 11 guests with futon sofas for flexible sleeping arrangements, and includes amenities such as a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, and 1 off-street parking space with free street parking.

Choose the Right Vacation Rentals with a Pool in Winthrop, MA

A vacation rental with a pool in Winthrop, MA is the ideal way to complement your daily coastal adventures.

Hyatus Luxury Residences Boston Everett Signature Collection - Winthrop, MA
10 5 reviews
Winthrop, MA
08/14 – 08/21
$1147/nighttotal: $8029 (7 )

Hyatus Luxury Residences Boston Everett Signature Collection

3 10
apartment , Everett
The Hyatus Luxury Residences Boston Everett Signature Collection is situated in Everett, 2.2 miles from Cambridge College and 3.7 miles from North Station and TD Garden.
This spacious 6,460 sq ft residence accommodates up to 7 guests with 1 bedroom, a living room, a private terrace, bar, and barbecue, plus access to a seasonal outdoor pool and on-site fitness center.
Elite Resort Home  Pool, Jacuzzi, Basketball  Sleeps 16+ King Bedsshuttle - Winthrop, MA
Winthrop, MA
08/14 – 08/21
$1353/nighttotal: $9471 (7 )

Elite Resort Home Pool, Jacuzzi, Basketball Sleeps 16+ King Bedsshuttle

3 10
apartment , Everett
This Everett condo offers a professionally managed luxury retreat with 5-star amenities, conveniently located within 3 miles of the Museum of Science, Boston Museum of Fine Arts, Encore Boston Harbor, and TD Garden.
This 1500 sq ft dwelling accommodates up to 16 guests with 3 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, terrace, garden, concierge, tennis court, and parking.

Top-Rated Oceanfront Vacation Rentals in Winthrop, MA

Relax near the shore in these coastal Winthrop, MA vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.

New Downtown Boston | Game Room Free Parking Fifa - Winthrop, MA
Winthrop, MA
08/14 – 08/21
$1657/nighttotal: $11599 (7 )

New Downtown Boston | Game Room Free Parking Fifa

3 10
apartment , Boston
Family-friendly 3br  Easy Blue Line Access Near Boston - Winthrop, MA
10 3 reviews
Winthrop, MA
08/14 – 08/21
$678/nighttotal: $4746 (7 )

Family-friendly 3br Easy Blue Line Access Near Boston

3 10
apartment , Boston

Traveler-Approved Luxury Vacation Rentals in Winthrop, MA

Refined interiors and prime locations make these luxury waterfront vacation rentals in Winthrop, MA the ideal choice for your stay.

Arcade | Air Hockey | Modern With Balcony - Winthrop, MA
9.9 526 reviews
Winthrop, MA
08/14 – 08/21
$601/nighttotal: $4207 (7 )

Arcade | Air Hockey | Modern With Balcony

2 10
apartment , Everett

Explore Vacation Rentals with Saunas in Winthrop, MA

Relax in style with an on-site sauna at these premium Winthrop, MA vacation rentals near the water.

30-3 - 3br Boston - Cozy Apt Near Franklin Park Zoo - Winthrop, MA
8.5 12 reviews
Winthrop, MA
08/14 – 08/21
$667/nighttotal: $4669 (7 )

30-3 - 3br Boston - Cozy Apt Near Franklin Park Zoo

3 10
apartment , Boston
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