Compare Vacation Rentals & Airbnb in Winthrop, MA

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

Best family friendly Winthrop, MA vacation rentals

Among the 179 accommodations in Winthrop, MA, here are the 4 best family friendly rentals

Family & Group Haven Near Downtown Retreat - Winthrop, MA
9.1 93 reviews
Winthrop, MA
14/08 – 21/08
$733/nighttotal: $5131 (7 )

Family & Group Haven Near Downtown Retreat

1 10
apartment , Boston
This five-bedroom Boston house, situated in Dorchester, is an eight-minute drive from the University of Massachusetts Boston and under a fifteen-minute drive from Fenway Park.
Sleeping fourteen guests, this spacious property boasts a well-equipped kitchen with modern appliances, a private deck, in-unit laundry, ample parking for three cars, and a dedicated workspace.
Elite Resort Home  Pool, Jacuzzi, Basketball  Sleeps 16+ King Bedsshuttle - Winthrop, MA
Winthrop, MA
14/08 – 21/08
$1891/nighttotal: $13237 (7 )

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

3 10
apartment , Everett
This professionally managed luxury flat in Everett offers a 5-star retreat with seamless check-in and tailored concierge services, conveniently situated within 5 kilometres of Boston's Museum of Science and Museum of Fine Arts, and easily accessible to Encore Boston Harbor and TD Garden.
This spacious 139-square-metre residence accommodates up to 16 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, tennis court, and parking, ensuring a hotel-style hospitality experience with the privacy of home.
Whole House Privacy, Yard/parking, 5min To Boston - Winthrop, MA
9.8 75 reviews
Winthrop, MA
14/08 – 21/08
$830/nighttotal: $5810 (7 )

Whole House Privacy, Yard/parking, 5min To Boston

4 10
house , Everett
This recently renovated four-bedroom house in Everett, Massachusetts, is conveniently located near major highways, providing easy access to Boston's North End (16-24km) and Salem (approx. 24km), as well as beaches within a 48km radius.
The property offers ample space for up to 10 guests, boasting a fully equipped kitchen with integrated laundry, a private garden with cafe seating, driveway parking for two cars, and proximity to Everett's walking/biking trails and river access for kayaking.
Stylish 6-bedroom Home Near Boston  Dual Units, Yard & Parking Included! - Winthrop, MA
9.8 34 reviews
Winthrop, MA
14/08 – 21/08
$1001/nighttotal: $7007 (7 )

Stylish 6-bedroom Home Near Boston Dual Units, Yard & Parking Included!

1 10
apartment , Everett
This spacious house is located in Everett, just a short distance from popular attractions like Encore Boston Harbor and TD Garden, making it a great base for exploring the city. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The property has six bedrooms, covering 232 square metres, making it perfect for large groups or families. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private patio, a garden, and a spa, ensuring a comfortable and enjoyable stay.

Best Winthrop, MA vacation rentals with a pool

Among the 179 accommodations in Winthrop, MA, here are the 1 best rentals with a pool

Hyatus Luxury Residences Boston Everett Signature Collection - Winthrop, MA
10 5 reviews
Winthrop, MA
14/08 – 21/08
$1604/nighttotal: $11228 (7 )

Hyatus Luxury Residences Boston Everett Signature Collection

3 10
apartment , Everett
This Everett flat is located 3.6 kilometres from Cambridge College and 5.9 kilometres from North Station and TD Garden, with Boston Logan International Airport a mere 4 kilometres away.
This pet-friendly apartment offers 600 square metres of space for up to 7 guests, featuring a private terrace, bar, barbecue facilities, air conditioning, a fully equipped kitchen with a refrigerator and coffee machine, a communal lounge, a swimming pool, and on-site fitness centre, with free Wi-Fi throughout.

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.

Destinations nearby

Best Winthrop, MA vacation rentals with a balcony

The Maverick Upstairs - New! - Lux Apartment - 2 Miles From Airport & Downtown Boston - Winthrop, MA
Winthrop, MA
14/08 – 21/08
$811/nighttotal: $5677 (7 )

The Maverick Upstairs - New! - Lux Apartment - 2 Miles From Airport & Downtown Boston

1 10
apartment , Chelsea
This Chelsea flat offers convenient access to Boston's North Station, TD Garden, and Logan Airport, situated approximately 1.9 kilometres away.
This spacious 120 square metre apartment accommodates up to 19 guests, featuring a fully equipped kitchen with a dishwasher and microwave, air conditioning, complimentary WiFi, and a private patio with an outdoor dining area.
5 Bedroom Historic Home Minutes To Boston With Yard - Winthrop, MA
10 12 reviews
Winthrop, MA
14/08 – 21/08
$1534/nighttotal: $10738 (7 )

5 Bedroom Historic Home Minutes To Boston With Yard

5 10
apartment , Medford
This five-bedroom Medford property, approximately 6.4 kilometres from Boston, offers easy access to Assembly Row and Station Landing, and is a three-minute walk from a local park and playground.
The 186-square-metre house features a newly renovated sunroom, a private garden with patio and gas grill, ample parking, and sleeps up to twelve guests, with all modern conveniences including a fully equipped kitchen and five queen-sized bedrooms.
Spacious 5br Home In Malden With Ac & Heat - Winthrop, MA
Winthrop, MA
14/08 – 21/08
$1116/nighttotal: $7812 (7 )

Spacious 5br Home In Malden With Ac & Heat

1 10
apartment , Malden
This Malden flat is situated 5.4 kilometres from Cambridge College and 7.7 kilometres from Boston North Station, offering convenient access to the city.
This five-bedroom residence accommodates up to nineteen guests, featuring a fully equipped kitchen, complimentary WiFi, private parking, air conditioning, and a balcony, with pets welcome.
233-1 4br Boston - Cozy Apt Near Mbta Station - Winthrop, MA
9.4 6 reviews
Winthrop, MA
14/08 – 21/08
$1996/nighttotal: $13972 (7 )

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

4 10
apartment , Boston
This family-friendly Boston apartment, situated approximately 5-6 kilometres from attractions such as the John F. Kennedy Presidential Library and Museum, the Museum of Fine Arts, Boston South Station, and Back Bay, offers convenient access to major sights whilst maintaining a peaceful residential atmosphere.
This spacious 149-square-metre dwelling boasts four bedrooms, two bathrooms, and can comfortably accommodate up to 23 guests, featuring a fully equipped kitchen, private terrace, free parking, Wi-Fi, and 24-hour concierge service.

Best Winthrop, MA vacation rentals with parking

Brand-new Spacious 4 Bedroom Home, Minutes From Train Station, Free St Parking - Winthrop, MA
8.6 19 reviews
Winthrop, MA
14/08 – 21/08
$956/nighttotal: $6692 (7 )

Brand-new Spacious 4 Bedroom Home, Minutes From Train Station, Free St Parking

4 10
apartment , Boston
This Dorchester property is situated 1 kilometre from Franklin Park Zoo and within 5 kilometres of the University of Massachusetts Boston and Boston Medical Centre.
This four-bedroom, three-bathroom house sleeps ten guests and boasts a fully equipped kitchen, Smart TV, free Wi-Fi, and convenient access to public transport, making it ideal for family trips or group getaways to Boston.
Sage Apartments Boston Logan Airport Chelsea - Winthrop, MA
Winthrop, MA
14/08 – 21/08
$1493/nighttotal: $10451 (7 )

Sage Apartments Boston Logan Airport Chelsea

2 10
apartment , Chelsea
Sage Apartments Boston Logan Airport Chelsea is located in the Chelsea district, just 1.9 kilometres from Logan Airport and 5.8 kilometres from the Freedom Trail. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
Each apartment has a fully equipped kitchen with a dishwasher and oven, allowing guests to prepare their own meals. Guests can also enjoy free parking, Wi-Fi, a fitness room, and a private bathroom with amenities.
Spacious 6br 2unit Near Downtown - Winthrop, MA
9.0 4 reviews
Winthrop, MA
14/08 – 21/08
$1514/nighttotal: $10598 (7 )

Spacious 6br 2unit Near Downtown

6 10
apartment , Boston
This six-bedroom Dorchester flat, near Upham's Corner station (a 1.6km walk), offers easy access to Franklin Park Zoo (4.8km), the John F. Kennedy Presidential Library and Museum (9.6km), and Boston Common (11.2km).
Sleeping sixteen guests, the property includes two bathrooms, Wi-Fi, air conditioning, laundry facilities, and essential amenities; explore Boston's attractions, including the New England Aquarium and Museum of Science, or enjoy nearby Boston Harbour and Flynn Cruiseport Boston.
Heart Of Southie - Hot Tub + Walk To Top Bars - Winthrop, MA
9.9 110 reviews
Winthrop, MA
14/08 – 21/08
$1604/nighttotal: $11228 (7 )

Heart Of Southie - Hot Tub + Walk To Top Bars

1 10
apartment , Boston
This four-bedroom house in South Boston is just a short walk from the beach and within easy reach of bars and restaurants, making it ideal for exploring the city. The property has received excellent ratings for location, cleanliness and overall user experience.
The house is spread over three floors and can comfortably accommodate up to 13 guests. With a fully equipped kitchen, a hot tub, a garden, and secure parking, this house offers everything you need for a relaxing and enjoyable stay.
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