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

Luxe 4bdr2ba Near Boston- T-station & Encore Casino - Winthrop, MA
10 5 reviews
Winthrop, MA
22/09 – 23/09
$875/nightfor 1 night

Luxe 4bdr2ba Near Boston- T-station & Encore Casino

4 2
apartment , Boston
This Somerville apartment, near a T-station providing easy access to Boston and Cambridge, is a 10-minute walk from Cambridge College and 3.2km from Boston North Station and TD Garden.
This 16-square-metre flat offers two bathrooms, sleeps 15 guests, includes a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, private parking, and a balcony; enjoy nearby Inman Square.
The Maverick - Luxurious Apartment - Near Airport/downtown - Winthrop, MA
9.2 13 reviews
Winthrop, MA
19/08 – 28/08
$816/nighttotal: $7344 (9 )

The Maverick - Luxurious Apartment - Near Airport/downtown

5 2
apartment , Chelsea
This five-bedroom Chelsea house, a 10-minute walk from Chelsea station and 1.6 miles from Suffolk University, offers easy access to public transport and local attractions including Encore Boston Harbor (3.7km) and Revere Beach (4.8km).
The 130 square metre property features a fully equipped kitchen, garden, parking, and accommodates up to 10 guests, boasting a terrace, air conditioning, and free Wi-Fi.
Amazing Location In Little Italy With Roof Deck - Winthrop, MA
10 78 reviews
Winthrop, MA
19/08 – 28/08
$675/nighttotal: $6075 (9 )

Amazing Location In Little Italy With Roof Deck

1 2
apartment , Boston
This Boston North End apartment, situated on the site of Paul Revere's former bell foundry, is less than 1.6km from the Freedom Trail, TD Garden, and the subway.
The one-bedroom flat sleeps two, boasting a fully equipped kitchen with stainless steel appliances, a roof deck with a hot tub and grill offering stunning harbour views, and proximity to numerous attractions including Faneuil Hall and Quincy Market.
Elegant Oasis With Pool And Gym - Winthrop, MA
10 9 reviews
Winthrop, MA
19/08 – 28/08
$553/nighttotal: $4977 (9 )

Elegant Oasis With Pool And Gym

2 2
apartment , Everett
This Everett apartment, conveniently located near Encore Boston Harbour (a 4-minute drive) and Assembly Row (a 6-minute drive), offers easy access to Chelsea station (a 14-minute walk).
The 93-square-metre (1000 square foot) self-catering property features two bedrooms, one bathroom, sleeps six, and includes a swimming pool, spa, garden, parking, and in-unit amenities such as a dishwasher, microwave, and laundry facilities.

Best Winthrop, MA vacation rentals with a pool

Among the 179 accommodations in Winthrop, MA, here are the 4 best rentals with a pool

The Dazzling Two-bedroom Two-bath Suite In Boston - Winthrop, MA
Winthrop, MA
22/09 – 23/09
$2212/nightfor 1 night

The Dazzling Two-bedroom Two-bath Suite In Boston

1 2
apartment , Boston
This two-bedroom suite is situated in Boston, 1.0 kilometre from South Station and 0.97 kilometres from Back Bay, offering convenient access to attractions such as the Boston Tea Party Ship & Museum and the Freedom Trail.
Boasting 111 square metres of floor area, this flat accommodates up to 13 guests with two bathrooms, a fully equipped kitchen, air conditioning, a fireplace, and on-site amenities including a swimming pool, fitness centre, and garden, with complimentary WiFi and lift access.
Boston 2 Bedroom Suite - Winthrop, MA
Winthrop, MA
22/09 – 23/09
$2733/nightfor 1 night

Boston 2 Bedroom Suite

2 2
apartment , Boston
This accessible two-bedroom, two-bathroom flat is situated in Boston's South End, offering immediate access to major attractions, markets, and parks within walking distance.
This 111 square metre residence accommodates up to eight guests and features a versatile living room with a sofa bed, a well-equipped kitchen, a primary suite with a large tub, and a second bedroom with a cot, ensuring a comfortable stay with amenities such as a swimming pool, garden, and parking.
Stylish 1br In Assembly Square | Pool, Gym & Views - Winthrop, MA
10 3 reviews
Winthrop, MA
19/08 – 28/08
$748/nighttotal: $6732 (9 )

Stylish 1br In Assembly Square | Pool, Gym & Views

5 2
apartment , Somerville
This Somerville flat is situated in the centre, a 5-minute walk from Assembly Row and LEGOLAND Discovery Centre, with Assembly Station just 200 metres away for excellent public transport links.
This 56 square metre dwelling offers accommodation for up to 4 guests, featuring 5 bedrooms, a fully equipped kitchen, air conditioning, a swimming pool, a garden, and a pool table for entertainment.
Family Fun In Boston: Rooftop Pool & City Views - Winthrop, MA
Winthrop, MA
19/08 – 28/08
$1299/nighttotal: $11691 (9 )

Family Fun In Boston: Rooftop Pool & City Views

1 2
apartment , Boston
This South End, Boston penthouse flat is conveniently located near the Museum of Fine Arts and Boston Harbour.
The 70 square metre (753 square feet) property, sleeping three, boasts a bedroom, bathroom, kitchen with fridge, microwave, and dishwasher, plus Wi-Fi, air conditioning, parking, and a swimming pool; nearby attractions include the TD Garden and Encore Boston Harbor.

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

Prime Seaport 2br Steps To Convention Center - Winthrop, MA
Winthrop, MA
22/09 – 23/09
$1280/nightfor 1 night

Prime Seaport 2br Steps To Convention Center

2 2
apartment , Boston
This Seaport District flat is ideally situated for convention attendees and those wishing to explore Boston's waterfront, offering a short walk to the Boston Convention and Exhibition Centre and proximity to attractions such as the Boston Tea Party Ship and Museum, as well as Boston South Station, with Custom House and Old State House within 2.4 kilometres.
This air-conditioned two-bedroom apartment accommodates up to seven guests and features a fully equipped kitchen, complimentary Wi-Fi, private on-site parking, and a private terrace, with Pleasure Bay Beach located 2.7 kilometres away.
Boston Gem: 1br Apartment With Pool - Winthrop, MA
Winthrop, MA
22/09 – 23/09
$2103/nightfor 1 night

Boston Gem: 1br Apartment With Pool

1 2
apartment , Boston
This South End flat is conveniently located near Boston's major attractions, offering easy access to Faneuil Hall Marketplace and Fenway Park.
The one-bedroom apartment sleeps five, featuring a queen-size bed, two futons, a fully equipped kitchen with dishwasher, a bathroom with bidet, and access to a swimming pool, parking, and a fitness room; Wi-Fi is included.
Casino Near - Winthrop, MA
Winthrop, MA
22/09 – 23/09
$479/nightfor 1 night

Casino Near

3 2
apartment , Malden
This Malden flat offers convenient access to Cambridge College, located 6.1 kilometres away, and Inman Square, 8.4 kilometres distant, with Logan Airport a mere 8 kilometres from your doorstep.
This family-friendly residence boasts 167 square metres of living space, featuring three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, complimentary WiFi, a balcony, a sun terrace, and private parking for up to five guests.
Charming & Stylish Studio On Beacon Hill #2 - Winthrop, MA
9.0 4082 reviews
Winthrop, MA
22/09 – 23/09
$683/nightfor 1 night

Charming & Stylish Studio On Beacon Hill #2

1 2
studio , Boston
This studio apartment is situated in the heart of Beacon Hill, just a short walk from Boston's main attractions, offering a prime location in a historic and charming neighbourhood. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a compact and comfortable studio, perfect for two guests, and comes equipped with a kitchenette, a private bathroom, and a flat-screen TV. You'll also have access to free Wi-Fi, air conditioning, and a balcony, making it a great base for exploring the city.

Best Winthrop, MA vacation rentals with parking

14a-cozy And Well Decorated Apartment In Awesome Boston - Winthrop, MA
10 32 reviews
Winthrop, MA
22/09 – 23/09
$987/nightfor 1 night

14a-cozy And Well Decorated Apartment In Awesome Boston

3 2
apartment , Boston
This Dorchester apartment, situated near Savin Hill station and less than 1.6km from the University of Massachusetts Boston, offers easy access to public transport and major attractions.
Sleeping up to 13 guests, this three-bedroom, two-bathroom property boasts a garden, private patio, parking, and modern amenities including Wi-Fi, a fully equipped kitchen, and a washing machine.
3br Pet-friendly Boston Apartment W/parking  Near Franklin Park Zoo 30/3 - Winthrop, MA
9.0 20 reviews
Winthrop, MA
22/09 – 23/09
$749/nightfor 1 night

3br Pet-friendly Boston Apartment W/parking Near Franklin Park Zoo 30/3

3 2
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.
Spacious North End 1 Br | 1ba - Winthrop, MA
9.9 62 reviews
Winthrop, MA
19/08 – 28/08
$515/nighttotal: $4635 (9 )

Spacious North End 1 Br | 1ba

1 2
apartment , Boston
This Boston North End apartment, situated on the corner of Fleet and North Streets, is a short walk (less than 1.5 km) from Hanover Street's restaurants, the Boston waterfront, Faneuil Hall Marketplace, and the New England Aquarium.
The ground-floor flat offers one bedroom, one bathroom, sleeps three guests, and features a modern kitchen with stainless steel appliances, a 50" Smart TV, central air conditioning, and access to a shared roof deck; in-building laundry is also available.
World Cup 2026 Revere Beach 1br Boston Stay - Winthrop, MA
9.8 158 reviews
Winthrop, MA
19/08 – 28/08
$246/nighttotal: $2214 (9 )

World Cup 2026 Revere Beach 1br Boston Stay

1 2
apartment , Revere
This Revere apartment, ideally situated for exploring the city, offers a one-bedroom flat sleeping up to four guests.
The self-catering property features an open-plan living area with a folding room divider, a queen-size bed, a twin day bed with a trundle, a fully equipped kitchen including a dishwasher, and on-site parking for one car.
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