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

The Day-burrill-wadsworth-la Voix House - Winthrop, MA
10 117 reviews

The Day-burrill-wadsworth-la Voix House

apartment, Winthrop Town
This Winthrop penthouse apartment, near Logan Airport, offers easy access to Boston city centre via bus or ferry, and is conveniently located close to Winthrop's beaches and a park with a skate park and playground.
The renovated three-bedroom dwelling boasts a private roof deck with stunning views, in-unit laundry, a sunroom, off-street parking including a Level 2 EV charger, and accommodates up to seven guests.
Studio Near Logan, Hot Tub & Private Entrance - Winthrop, MA
10 1 review

Studio Near Logan, Hot Tub & Private Entrance

studio, Boston
This newly refurbished studio flat, located a mere 5 minutes' drive from Logan International Airport and offering direct access to the city centre via the Blue Line, is ideal for exploring Boston.
This self-contained accommodation for up to four guests boasts a king Murphy bed, a queen sofa bed, a fully equipped kitchen, a private bathroom with a rain shower, a sunroom, a workspace, and shared access to a garden with a hot tub, fire pit, and barbecue.
Sunlit Luxury 2br | Beach/train Access + Boston - Winthrop, MA
10 21 reviews

Sunlit Luxury 2br | Beach/train Access + Boston

apartment, Revere
This Revere flat, situated a mere 300 meters from Revere Beach and a 3-minute walk to the train station, offers a 3.2-kilometer commute to Boston and is 16 kilometers from Logan Airport.
This family-friendly flat accommodates four guests with two bedrooms, a fully equipped kitchen, air conditioning, high-speed internet, and a dedicated workspace, complemented by nearby access to educational institutions.
Beautiful Beacon Hill 2 Bedroom! - Winthrop, MA
9.8 541 reviews

Beautiful Beacon Hill 2 Bedroom!

apartment, Boston
This Beacon Hill flat offers prime accommodation, situated a short walk from Boston Common, the Public Garden, and the Freedom Trail.
The two-bedroom apartment, sleeping four, includes a fully equipped kitchen, in-unit laundry, a living room with gas fireplace and Apple TV, and a bathroom with a spa shower/tub; nearby attractions include the Charles Street shops and Mass General Hospital.

Best Winthrop, MA vacation rentals with a pool

Among the 254 accommodations in Winthrop, MA, here are the 1 best rentals with a pool

Curated Designer Retreat  Pool  Gym  Dining - Winthrop, MA
9.9 107 reviews

Curated Designer Retreat Pool Gym Dining

apartment, Everett
This modern two-bedroom, two-bathroom flat in Everett offers easy access to Encore Boston Harbor and Assembly Row, with major motorways nearby for travel across Greater Boston.
Guests can enjoy a seasonal courtyard swimming pool (June-September), a 24/7 fitness centre, resident lounges, and co-working spaces, with an indoor pet wash station and a creative maker space also available.

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

(42l2) Celtics, Bruins! Lets Go! - Winthrop, MA
9.4 112 reviews

(42l2) Celtics, Bruins! Lets Go!

apartment, Boston
This West End flat is ideally located near Boston's North Station and TD Garden, offering easy access to public transport and major attractions.
The one-bedroom apartment sleeps four, features a fully equipped kitchen, and includes Celtics and Bruins themed décor; on-site parking is available via SpotHero (reservations required).

Best Winthrop, MA vacation rentals with parking

Gorgeous Beacon Hill 1br | 1ba - Winthrop, MA
9.9 373 reviews

Gorgeous Beacon Hill 1br | 1ba

apartment, Boston
This Beacon Hill flat is ideally located within walking distance of Boston Common, the Public Garden, and the Freedom Trail.
The one-bedroom apartment sleeps three, features a fully equipped kitchen, in-unit laundry, a 50" HDTV, and is close to Charles Street's shops and restaurants.
3 Bdr, Steps From The Ocean, Minutes From Boston - Winthrop, MA
9.6 62 reviews

3 Bdr, Steps From The Ocean, Minutes From Boston

apartment, Winthrop Town
This Winthrop Beach house, offering direct ocean views, enjoys easy bus access to Oriental Heights and Boston, approximately 8-10km away.
Sleeping five guests comfortably, this three-bedroom property boasts a fully equipped kitchen, laundry facilities, and private access; nearby amenities include local dining options.
Boston Beach Pad Logan Airport - Winthrop, MA
9.9 37 reviews

Boston Beach Pad Logan Airport

apartment, Winthrop Town
This Winthrop Town flat boasts an oceanfront location directly opposite Winthrop Beach, a 15-minute drive (approx. 24km) from Logan International Airport and 20 minutes (approx. 16km) from Boston Common.
The two-bedroom apartment, sleeping four, features a private deck with sea views, a fully equipped kitchen including a dishwasher, and smart projectors with streaming services; nearby attractions include Cafe Valenciano and Deer Island Park.
(42l5) Celtics Bruins Td Garden Outside Your Door! - Winthrop, MA
9.5 144 reviews

(42l5) Celtics Bruins Td Garden Outside Your Door!

apartment, Boston
This West End flat is ideally located near Boston's North Station and TD Garden, offering easy access to public transport and major sporting events.
The one-bedroom apartment sleeps four, features a fully equipped kitchen, and includes Celtics and Bruins themed décor; on-site parking is available via SpotHero (reservations required).
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