Best apartment offers in Winthrop, MA

172 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Winthrop, MA apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

172 Holiday apartments Winthrop, MA

Best family friendly Winthrop, MA Holiday Apartments and Self Catering Accommodations

Among the 172 accommodations in Winthrop, MA, here are the 4 best family friendly holiday apartments

30-1 - 4br Boston - Cozy Apt Near Geneva Cliffs - Winthrop, MA
9.2 10 reviews
Winthrop, MA
14/08 – 21/08
1009 €/nighttotal: 7063 € (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.
Chic 3br1.5ba City Stay - Near T + Parking - Winthrop, MA
Winthrop, MA
14/08 – 21/08
669 €/nighttotal: 4683 € (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.
Sage Apartments Boston Logan Airport Chelsea - Winthrop, MA
Winthrop, MA
14/08 – 21/08
924 €/nighttotal: 6468 € (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.
Lux 2br In Assembly Square | Pool & Fitness Center - Winthrop, MA
10 4 reviews
Winthrop, MA
18/10 – 24/10
572 €/nighttotal: 3432 € (6 )

Lux 2br In Assembly Square | Pool & Fitness Center

6 1
apartment , Somerville
This six-bedroom flat is centrally located in Somerville, a short walk of 500 meters from Assembly Row shopping and LEGOLAND Discovery Centre, with convenient five-minute access to the Assembly subway station for exploring Boston.
This 98 square meter residence accommodates up to five guests and features a communal swimming pool, garden, barbecue area, pool table, air conditioning, a well-equipped kitchen with a dishwasher, and in-unit laundry facilities.

Best Holiday Apartments and Self Catering Accommodations in Winthrop, MA with a pool

Among the 172 accommodations in Winthrop, MA, here are the 4 best apartments with a pool

Boston 2 Bedroom Suite - Winthrop, MA
Winthrop, MA
29/06 – 05/07
1313 €/nighttotal: 7878 € (6 )

Boston 2 Bedroom Suite

2 4
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.
Sterling 1br At Everett | Pool & Gym - Winthrop, MA
Winthrop, MA
29/06 – 05/07
300 €/nighttotal: 1800 € (6 )

Sterling 1br At Everett | Pool & Gym

5 4
apartment , Everett
This Everett flat is centrally located, offering a 3-kilometre drive to Encore Boston Harbor and a 5-kilometre drive to the shops and restaurants at Assembly Row.
This 46 square metre dwelling accommodates up to four guests and features a communal swimming pool, garden, billiards, and a fully equipped kitchen with a washer and dryer.
South End Escape Your Family's Dream Getaway - Winthrop, MA
Winthrop, MA
29/06 – 05/07
1064 €/nighttotal: 6384 € (6 )

South End Escape Your Family's Dream Getaway

1 4
apartment , Boston
This South End flat is a 16-minute walk from Boston South Station and 1.1 kilometres from Back Bay, placing you close to attractions such as the Freedom Trail and Boston Common.
This 111 square metre residence offers three bedrooms, two bathrooms, a fireplace, and a water park, with on-site amenities including a fitness centre and swimming pool, and allows pets.
Luxury Apartments By Hyatus At Boston Everett - Winthrop, MA
10 2 reviews
Winthrop, MA
29/06 – 05/07
2003 €/nighttotal: 12018 € (6 )

Luxury Apartments By Hyatus At Boston Everett

2 4
apartment , Everett
This Everett flat offers proximity to key destinations, situated within 4.8 kilometres of Encore Boston Harbor and Assembly Row, with Chelsea Station a 14-minute walk away.
This serviced apartment provides a swimming pool, fitness centre, and rooftop terrace, alongside in-unit laundry and complimentary public area Wi-Fi, with free on-site parking and gas grills for guest convenience.

Frequently asked questions about apartment rentals in Winthrop, MA

Destinations nearby

Best Winthrop, MA holiday apartments with air conditioning

Massive Luxury 4 Br Near Boston Cambridge Salem - Winthrop, MA
9.8 146 reviews
Winthrop, MA
18/10 – 30/10
305 €/nighttotal: 3660 € (12 )

Massive Luxury 4 Br Near Boston Cambridge Salem

1 5
apartment , Malden
This spacious Malden apartment, a 4-bedroom property perfect for families or groups, is situated approximately 2.5km from Malden Centre and offers easy access to Boston (a 16-minute drive) via public transport or car, with Assembly Row and Encore Boston Harbor casino also nearby.
The 4-bedroom, 1-bathroom dwelling boasts a fully equipped kitchen, including a dishwasher, private laundry facilities, keyless entry, and on-site parking, accommodating up to 8 guests and featuring a 65” Smart TV and high-quality memory foam mattresses.
30-3 - 3br Boston - Cozy Apt Near Franklin Park Zoo - Winthrop, MA
8.5 12 reviews
Winthrop, MA
14/08 – 21/08
577 €/nighttotal: 4039 € (7 )

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

3 10
apartment , Boston
This newly renovated three-bedroom apartment in Boston is conveniently located a short distance (approximately 2.9km) from Carson Beach and within 4.5km of the John F. Kennedy Presidential Library and Museum, the Museum of Fine Arts, and Boston South Station.
The 111-square-metre property boasts a spacious layout, accommodating up to 15 guests, with a fully equipped kitchen, private balcony, terrace, free Wi-Fi, free private parking, and concierge services.
Steps From Short Beach - Nahant - 3 Bedroom - Winthrop, MA
9.9 147 reviews
Winthrop, MA
18/10 – 24/10
420 €/nighttotal: 2520 € (6 )

Steps From Short Beach - Nahant - 3 Bedroom

3 1
apartment , Nahant
This apartment is located in Nahant, just a short walk from Short Beach and Doggy Beach, offering views of Boston's skyline and a peaceful, coastal escape. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment is a spacious three-bedroom property with one bathroom, comfortably accommodating up to six guests. It features a fully equipped kitchen, air conditioning, a garden, and parking, making it a perfect choice for families or groups looking for a relaxing and comfortable stay.
Boston Group 6br Sleeps 15 Near Downtown Parking - Winthrop, MA
9.9 17 reviews
Winthrop, MA
14/08 – 21/08
852 €/nighttotal: 5964 € (7 )

Boston Group 6br Sleeps 15 Near Downtown Parking

1 10
apartment , Boston
This spacious Boston apartment, near major universities and 6.3 km from Fenway Park, offers easy access to beaches (3.2 km away) and the city centre.
The self-catering property comprises two fully equipped units, sleeping up to 15 guests, with six bedrooms, two bathrooms, a garden, parking, high-speed Wi-Fi, and central air conditioning.

Best pet-friendly Winthrop, MA holiday apartments

Among the 172 accommodations in Winthrop, MA, here are the 4 best pet friendly holiday apartments

Airy 1br Walkable To Everywhere In Boston - Winthrop, MA
9.0 2 reviews
Winthrop, MA
18/10 – 24/10
344 €/nighttotal: 2064 € (6 )

Airy 1br Walkable To Everywhere In Boston

1 1
apartment , Boston
This Boston apartment, located less than 1.6km from Boston Common and within walking distance of the Freedom Trail, King's Chapel Burying Ground, and South Station, offers easy access to the city's historical attractions and transport links.
The 50 square metre flat comprises one bedroom, one bathroom, and can accommodate three guests; amenities include a fully equipped kitchen, in-unit laundry, air conditioning, free Wi-Fi, and free toiletries.
Family-friendly 3br  Easy Blue Line Access Near Boston - Winthrop, MA
10 3 reviews
Winthrop, MA
14/08 – 21/08
586 €/nighttotal: 4102 € (7 )

Family-friendly 3br Easy Blue Line Access Near Boston

3 10
apartment , Boston
This East Boston flat offers convenient access to Revere Beach, approximately 8 kilometres away, and Boston Common, just under 5 kilometres distant, placing you within easy reach of the New England Aquarium and Museum of Science.
This three-bedroom flat accommodates up to ten guests and includes amenities such as air conditioning, Wi-Fi, and a hairdryer, with nearby transport links providing access to TD Garden and Fenway Park for sporting events and concerts.
Curated Designer Retreat  Pool  Gym  Dining - Winthrop, MA
10 6 reviews
Winthrop, MA
29/06 – 05/07
463 €/nighttotal: 2778 € (6 )

Curated Designer Retreat Pool Gym Dining

6 4
apartment , Everett
This Everett flat is centrally located, offering convenient access to Encore Boston Harbor (approximately 640 metres) and LEGOLAND Discovery Center (approximately 960 metres).
This 92 square metre residence accommodates up to 5 guests with 6 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a swimming pool, garden, spa, and covered parking, with an 11:00 check-out time.
(42l5) Celtics Bruins Td Garden Outside Your Door! - Winthrop, MA
9.5 134 reviews
Winthrop, MA
29/06 – 05/07
248 €/nighttotal: 1488 € (6 )

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

1 4
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).
©2026 cozycozy.com