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

New-spacious 3br-office-game Room-laundry In Unit - Winthrop, MA
10 2 reviews
Winthrop, MA
14/08 – 21/08
$912/nighttotal: $6384 (7 )

New-spacious 3br-office-game Room-laundry In Unit

1 10
apartment, Everett
This Everett flat is located a 5-minute drive from Encore Boston Harbor and a 5-minute walk to the Route 109 bus stop, offering direct access to Sullivan Station and Boston.
This spacious 3-bedroom property accommodates up to 10 guests and features a fully equipped kitchen, in-unit laundry, a pool table, and one complimentary parking space.
The Maverick - Luxurious Apartment - Near Airport/downtown - Winthrop, MA
9.2 13 reviews
Winthrop, MA
14/08 – 21/08
$805/nighttotal: $5635 (7 )

The Maverick - Luxurious Apartment - Near Airport/downtown

5 10
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.
Hyatus Luxury Residences Boston Everett Premier Collection - Winthrop, MA
9.8 10 reviews
Winthrop, MA
14/08 – 21/08
$1355/nighttotal: $9485 (7 )

Hyatus Luxury Residences Boston Everett Premier Collection

4 10
apartment, Everett
This two-bedroom, two-bathroom flat in Everett is situated 4.5 kilometres from Cambridge College and 5.9 kilometres from North Station, with Boston Logan International Airport just 4 kilometres away.
This 93 square metre apartment accommodates up to nine guests and features air conditioning, complimentary Wi-Fi, a fully equipped kitchen with a fridge and microwave, a swimming pool, a bar, and a fitness centre.
3br Pet-friendly Boston Apartment W/parking  Near Franklin Park Zoo 30/3 - Winthrop, MA
9.0 20 reviews
Winthrop, MA
14/08 – 21/08
$811/nighttotal: $5677 (7 )

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

3 10
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.
Chic 3br1.5ba City Stay | Near T + Parking - Winthrop, MA
9.6 5 reviews
Winthrop, MA
14/08 – 21/08
$763/nighttotal: $5341 (7 )

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

3 10
apartment, Boston
This Dorchester apartment, situated a 0.8-1.6km walk from Savin Hill T station, provides easy access to Boston's attractions.
Sleeping up to 11 guests in a three-bedroom property with one bathroom, this Boston flat boasts a garden, parking, and amenities including a kitchen with dishwasher, plus internet access; nearby restaurants include the Mofongo Factory and Milkweed Café.
The Maverick Downstairs - Lux Apartment - Winthrop, MA
9.7 139 reviews
Winthrop, MA
14/08 – 21/08
$734/nighttotal: $5138 (7 )

The Maverick Downstairs - Lux Apartment

1 10
apartment, Chelsea
This modern four-bedroom flat is located in Chelsea, just 10 kilometres from Boston and the airport, making it a convenient base for exploring the city. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment comfortably sleeps 10 guests and features a fully equipped kitchen, a private garden, and parking. It also includes modern amenities such as air conditioning, a smart TV, and a dishwasher.
Arcade | Air Hockey | Modern With Balcony - Winthrop, MA
9.9 526 reviews
Winthrop, MA
14/08 – 21/08
$840/nighttotal: $5880 (7 )

Arcade | Air Hockey | Modern With Balcony

2 10
apartment, Everett
This newly renovated flat is located in Everett, just 3 kilometres from Boston Logan International Airport and 4 kilometres from the Encore Boston Harbor casino, making it a convenient base for exploring the city and its surroundings. The property has received excellent ratings for location, cleanliness, and overall user experience.
The two-bedroom apartment is well-equipped for a comfortable stay, with a fully equipped kitchen, high-speed Wi-Fi, a 4K TV with streaming services, and an arcade machine for entertainment. Guests can also enjoy a private garden and on-site parking.
Charming Boston Home, Near T - Winthrop, MA
9.8 52 reviews
Winthrop, MA
14/08 – 21/08
$1136/nighttotal: $7952 (7 )

Charming Boston Home, Near T

4 10
house, Boston
This South Boston property, a five-minute walk (0.8 km) from the T subway, offers easy access to Boston's attractions.
Sleeping up to twelve guests, this four-bedroom, two-bathroom house boasts an open-plan living, kitchen, and dining area, a shared patio, high-speed internet, and a fully equipped kitchen; nearby attractions and restaurants are within easy reach.
The Maverick Upstairs - Lux Apartment - Near Airport/downtown - New! - Winthrop, MA
9.4 3 reviews
Winthrop, MA
14/08 – 21/08
$805/nighttotal: $5635 (7 )

The Maverick Upstairs - Lux Apartment - Near Airport/downtown - New!

4 10
apartment, Chelsea
This modern four-bedroom flat in Chelsea offers excellent connectivity, being a 5-minute walk from public transport and a less than 10-minute journey to Boston and the airport.
This residence accommodates up to ten guests with its four bedrooms featuring memory foam queen beds, a sofa bed, a well-equipped kitchen, a private patio, and complimentary amenities including central heating and air conditioning.
Charming 4r Boston Home W/parking, 5 Min To Casino - Winthrop, MA
9.8 115 reviews
Winthrop, MA
14/08 – 21/08
$780/nighttotal: $5460 (7 )

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

4 10
apartment, Everett
This four-bedroom property is conveniently located in Everett, just a short drive or public transport ride from downtown Boston, Fenway Park, and Logan Airport. The apartment has received excellent ratings for its cleanliness, location, and overall user experience.
The spacious home features a dedicated office space, a comfortable living area, and a private master suite with its own bathroom. Guests can enjoy the convenience of a fully equipped kitchen, air conditioning, internet access, and a choice of outdoor spaces, including a covered front deck and a relaxing patio in the backyard.
Bright & Cozy Boston Stay | 3br + Free Parking - Winthrop, MA
9.8 10 reviews
Winthrop, MA
14/08 – 21/08
$828/nighttotal: $5796 (7 )

Bright & Cozy Boston Stay | 3br + Free Parking

3 10
apartment, Boston
This spacious three-bedroom flat offers convenient access to Boston's Downtown, Seaport, and North End districts, with Boston Logan International Airport a mere few minutes away by car.
This pet-friendly apartment provides off-street parking for two vehicles, a private rear deck, and accommodates up to eight guests with flexible sleeping arrangements, including a King bed, Queen bed, two Full beds, and a Twin-over-Twin bunk, all equipped with Smart TVs and a fully fitted kitchen.
2000sqft Modern&luxury 5min To Encore|10min To Bos - Winthrop, MA
9.8 686 reviews
Winthrop, MA
14/08 – 21/08
$813/nighttotal: $5691 (7 )

2000sqft Modern&luxury 5min To Encore|10min To Bos

3 10
apartment, Everett
This newly renovated luxury apartment is situated in Everett, just a short drive from Boston and the airport, with easy access to the Encore casino and the Wellington Orange Line train station. The property has received excellent ratings for its cleanliness, location and user experience.
The apartment offers three bedrooms and two bathrooms, making it perfect for families or groups. Guests can enjoy complimentary coffee, snacks, water, and hygiene kits, as well as two large 4K TVs with access to live TV channels and streaming services.

Best family friendly Winthrop, MA vacation rentals

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

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.
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.
30-1 - 4br Boston - Cozy Apt Near Geneva Cliffs - Winthrop, MA
9.2 10 reviews
Winthrop, MA
14/08 – 21/08
$1630/nighttotal: $11410 (7 )

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

4 10
apartment, Boston
This spacious Boston apartment, located near Carson Beach (2.9km) and convenient to the John F. Kennedy Presidential Library and Museum (4.5km) and the Museum of Fine Arts (6.1km), offers easy access to public transport via South Station (6.6km).
The 130 square metre property features four bedrooms, one bathroom, sleeps eighteen guests, includes a fully equipped kitchen, free Wi-Fi, private parking, and a terrace; making it ideal for families or large groups visiting the city.
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.

Best Winthrop, MA vacation rentals with a pool

Among the 179 accommodations in Winthrop, MA, here are the 2 best rentals with a pool

Elite Resort Home  Pool, Jacuzzi, Basketball  Sleeps 16+ King Bedsshuttle - Winthrop, MA
2.0 1 review
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.
Hyatus Luxury Residences Boston Everett Marquis Collection - Winthrop, MA
9.6 12 reviews
Winthrop, MA
14/08 – 21/08
$1565/nighttotal: $10955 (7 )

Hyatus Luxury Residences Boston Everett Marquis Collection

4 10
apartment, Everett
The Hyatus Luxury Residences Boston Everett Marquis Collection is situated in Everett, 4.5 kilometres from Cambridge College and 5.7 kilometres from North Station and TD Garden.
This two-bedroom flat offers 93 square metres of living space for up to nine guests, featuring air conditioning, a fully equipped kitchen with a refrigerator and coffee machine, two bathrooms, a swimming pool, a bar, a fitness centre, and complimentary Wi-Fi.

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

Chic 3br1.5ba City Stay - Near T + Parking - Winthrop, MA
Winthrop, MA
14/08 – 21/08
$1081/nighttotal: $7567 (7 )

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

3 10
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.
The Maverick Downstairs - Lux Apartment - Close To Downtown Boston & Airport - Winthrop, MA
9.2 21 reviews
Winthrop, MA
14/08 – 21/08
$811/nighttotal: $5677 (7 )

The Maverick Downstairs - Lux Apartment - Close To Downtown Boston & Airport

4 10
apartment, Chelsea
This Chelsea apartment is just 3.2 kilometres from Boston Logan Airport and within 4.8 kilometres of attractions like the Freedom Trail, Boston North Station, and TD Garden. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travellers seeking a comfortable and convenient stay.
The apartment has four bedrooms, one bathroom, and a floor area of 130 square metres, accommodating up to 10 guests. Guests can enjoy a fully equipped kitchen, a patio and terrace, free parking, free Wi-Fi, and laundry service.
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.
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.

Best Winthrop, MA vacation rentals with parking

85a Charming, Cozy 3br, 2ba Home Near Downtown Boston - Winthrop, MA
9.6 7 reviews
Winthrop, MA
14/08 – 21/08
$1106/nighttotal: $7742 (7 )

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

3 10
apartment, Boston
This Dorchester, Boston apartment is conveniently located a short drive (approximately 3.2km) from Franklin Park Zoo and the Samuel Adams Brewery, and within a 12-13 minute walk of two subway stations offering easy access to Boston's attractions.
This three-bedroom, two-bathroom dwelling sleeps up to twelve guests and includes amenities such as free Wi-Fi, on-site parking, a fully equipped kitchen with dishwasher, in-unit laundry, and air conditioning.
Pet-friendly Boston Home W/ Parking, 5 Min To Franklin Park Zoo 233/3 - Winthrop, MA
8.8 38 reviews
Winthrop, MA
14/08 – 21/08
$1044/nighttotal: $7308 (7 )

Pet-friendly Boston Home W/ Parking, 5 Min To Franklin Park Zoo 233/3

4 10
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.
Peaceful, Modern 3br Home Near Encore Casino, 12min To Boston - Winthrop, MA
Winthrop, MA
14/08 – 21/08
$1051/nighttotal: $7357 (7 )

Peaceful, Modern 3br Home Near Encore Casino, 12min To Boston

3 10
apartment, Everett
This renovated three-bedroom flat at 51 Paris Street in Everett, MA, is conveniently situated approximately 800 metres from Encore Boston Harbor Casino and about 19 kilometres from Downtown Boston.
This accommodation offers space for up to 10 guests with three bedrooms, one bathroom, a fully equipped kitchen including a fridge, microwave oven, and dishwasher, air conditioning, in-unit laundry, and two off-street parking spaces, with pets welcome.
Historic And Charming Brownstone - Winthrop, MA
9.8 58 reviews
Winthrop, MA
14/08 – 21/08
$2221/nighttotal: $15547 (7 )

Historic And Charming Brownstone

4 10
apartment, Boston
This Charlestown holiday home is situated less than 1.6km from the Bunker Hill Monument and within a 4.8km radius of Boston attractions including the Museum of Science, TD Garden, and Boston Common.
The 238 square metre property boasts four bedrooms, three bathrooms, sleeps ten guests, and includes a fully equipped kitchen, private yard, balcony, and free Wi-Fi in communal areas.
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