Search vacation rentals in Winthrop, MA from 100+ sites!

179 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Winthrop, MA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Winthrop, MA

Best Winthrop, MA vacation rentals with a balcony

Waterfront Escape - Close To Airport & Downtown - Winthrop, MA
9.8 4 reviews
Winthrop, MA
09/22 – 09/23
$1876/nightfor 1 night

Waterfront Escape - Close To Airport & Downtown

4 2
house , Boston
This waterfront Boston house, near Constitution Beach, is 3.4 miles from North Station, TD Garden, and the Freedom Trail.
This 2600-square-foot villa features one bedroom, four bathrooms, accommodates up to 19 guests, and includes a fully equipped kitchen, private terrace, free Wi-Fi, and on-site parking.
Boston Pad: 2br Suite With Pool And Gym - Winthrop, MA
10 1 review
Winthrop, MA
09/22 – 09/23
$1879/nightfor 1 night

Boston Pad: 2br Suite With Pool And Gym

2 2
apartment , Boston
This luxurious two-bedroom suite in Boston's South End offers easy access to Fenway Park, Quincy Market, the New England Aquarium, and the Museum of Science.
The 1190-square-foot apartment features two bathrooms, sleeps five guests, and includes a full kitchen, in-unit laundry, and access to a swimming pool and terrace.
Boston Family Suite With Pool And Gym: Exquisite For Families - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$1730/nightfor 1 night

Boston Family Suite With Pool And Gym: Exquisite For Families

2 2
apartment , Boston
This two-bedroom, two-bathroom condo is located in Boston's South End, offering convenient access to markets, parks, and museums.
This handicapped-accessible unit spans 1190 square feet and accommodates up to 7 guests, featuring a full kitchen, air conditioning, a swimming pool, terrace, garden, and parking.
Pet-friendly Boston Home W/ Parking, 5 Min To Franklin Park Zoo 233/3 - Winthrop, MA
9.0 37 reviews
Winthrop, MA
09/22 – 09/23
$785/nightfor 1 night

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

4 2
apartment , Boston
This Boston apartment is conveniently located near Franklin Park Zoo, just a short drive from the Arnold Arboretum and about 15 minutes from downtown Boston and Fenway Park. The apartment has received excellent ratings for cleanliness and location, making it an ideal choice for travelers looking for a comfortable and convenient stay.
This spacious home has four bedrooms and two bathrooms, comfortably accommodating up to 13 guests. The apartment features modern amenities, including a fully equipped kitchen, washer and dryer, high-speed internet, and a private parking spot for two vehicles.

Browse Family-Friendly Vacation Rentals in Winthrop, MA

Find the perfect family vacation rental or Airbnb in Winthrop, MA with plenty of room to spread out near local beaches.

Stylish 1br In Assembly Square | Pool, Gym & Views - Winthrop, MA
10 3 reviews
Winthrop, MA
08/19 – 08/28
$535/nighttotal: $4815 (9 )

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

5 2
apartment , Somerville
This Somerville apartment is located downtown, a 5-minute walk from Assembly Row and LEGOLAND Discovery Center, with Assembly subway station just a 2-minute walk away.
This 600 sq ft dwelling accommodates up to 4 guests with 5 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, a swimming pool, garden with barbecue, and on-site billiards.
Family Fun In Boston: Rooftop Pool & City Views - Winthrop, MA
Winthrop, MA
08/19 – 08/28
$929/nighttotal: $8361 (9 )

Family Fun In Boston: Rooftop Pool & City Views

1 2
apartment , Boston
This South End Boston penthouse offers convenient access to the Museum of Fine Arts and Boston Seaport.
The 750-square-foot one-bedroom apartment sleeps three, featuring a full kitchen, in-unit Wi-Fi, and a dedicated workspace; nearby attractions include TD Garden and Encore Boston Harbor.
Elegant 2br - 2ba Oasis With Pool & Gym - Winthrop, MA
10 3 reviews
Winthrop, MA
08/19 – 08/28
$421/nighttotal: $3789 (9 )

Elegant 2br - 2ba Oasis With Pool & Gym

3 2
apartment , Everett
This Everett apartment rental is conveniently located near Encore Boston Harbor and Assembly Row, a short drive away, and a 14-minute walk from Chelsea Station.
This 1,000-square-foot apartment sleeps six guests comfortably, boasting six bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, in-unit laundry, a swimming pool, and free Wi-Fi.
Luxe 4bdr2ba Near Boston- T-station & Encore Casino - Winthrop, MA
10 5 reviews
Winthrop, MA
09/22 – 09/23
$626/nightfor 1 night

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

4 2
apartment , Boston
This Somerville apartment rental is conveniently located near a T-station, providing easy access to Boston and Cambridge, a 10-minute walk from Cambridge College, and approximately 2 miles from Boston's North Station and TD Garden.
This 170-square-foot apartment sleeps up to 15 guests and boasts two bathrooms, a fully equipped kitchen with a dishwasher, in-unit laundry, free Wi-Fi, private parking, and a balcony; nearby attractions include Inman Square.

Frequently Asked Questions about vacation rentals in Winthrop, MA

  • What are the top family-friendly attractions in Winthrop, MA?

    The Winthrop Beach is a great place to spend a day with the family. There's also a playground at the Winthrop Shore Reservation, and the Winthrop Public Library has a great children's section.
  • What are the best Airbnb and vacation rentals 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. You'll want to book early though, as rentals tend to fill up fast.
  • What are the most popular Airbnbs in Winthrop, MA?

  • What are the best budget-friendly activities in Winthrop, MA?

    Take a walk along the Winthrop Shore Reservation, it's a great way to get some exercise and enjoy the views. You can also visit the Winthrop Public Library, which has a great selection of books and other resources.
  • What are the best vacation rentals with a pool in Winthrop, MA?

  • What are the best restaurants with local dishes in Winthrop, MA?

    The Winthrop Fish Market is a great place to get fresh seafood. There's also a lot of great Italian food in Winthrop, like the restaurant called The Italian Kitchen.
  • What are the best rentals for families and kids in Winthrop, MA?

  • What are the best walking or cycling routes in Winthrop, MA?

    The Winthrop Shore Reservation has a great walking and cycling path that runs along the waterfront. You can also take a scenic bike ride through the residential streets of Winthrop.
  • 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.

  • Are there pet-friendly attractions in Winthrop, MA?

    The Winthrop Shore Reservation is pet-friendly, and there are many dog-friendly beaches in the area. You can also find some pet-friendly restaurants in Winthrop.
  • What are the benefits of choosing a vacation rental in Winthrop, MA?

    Vacation rentals in Winthrop offer more space and privacy than hotels. They often come with amenities like a kitchen and laundry facilities, which can be helpful for families or groups. You can also find vacation rentals in a variety of locations, from beachfront properties to homes in quieter neighborhoods.
  • What are the top sports attractions and facilities in Winthrop, MA?

    Winthrop has a few different sports facilities, including the Winthrop High School athletic fields and the Winthrop YMCA. The town also has a few different beaches that are great for swimming, sunbathing, and surfing.

Destinations nearby

Best Winthrop, MA vacation rentals with parking

Prime Central 1brm In North End Boston - Winthrop, MA
9.8 219 reviews
Winthrop, MA
08/19 – 08/28
$332/nighttotal: $2988 (9 )

Prime Central 1brm In North End Boston

1 2
apartment , Boston
This Boston apartment is located in the North End, a historic neighborhood within easy walking distance of popular attractions like Paul Revere House, TD Garden, and the New England Aquarium. The apartment has received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom unit comfortably accommodates up to three guests. The apartment includes modern amenities like free Wi-Fi, a fully equipped kitchen, a TV, and parking, making it a convenient and enjoyable place to stay.
Up To 30% Off  Spacious 4br Boston Home W/ Free Parking, Pet-friendly 30/1 - Winthrop, MA
9.2 14 reviews
Winthrop, MA
09/22 – 09/23
$629/nightfor 1 night

Up To 30% Off Spacious 4br Boston Home W/ Free Parking, Pet-friendly 30/1

4 2
apartment , Boston
This Dorchester, Boston rental is conveniently located near downtown Boston (a 10-15 minute drive), Fenway Park, and Logan Airport.
This spacious four-bedroom house sleeps twelve guests, features a fully equipped kitchen, private backyard, assigned parking for two cars, and modern amenities including smart TVs, SONOS soundbars, and high-speed Wi-Fi.
Cozy & Modern Entire Home - Winthrop, MA
10 2 reviews
Winthrop, MA
08/19 – 08/28
$351/nighttotal: $3159 (9 )

Cozy & Modern Entire Home

2 2
apartment , Winthrop Town
This Winthrop apartment offers easy access to Winthrop Beach and Yirrell Beach, located just a 5-minute walk away, and is a 20-mile drive from Boston's attractions, with Logan Airport and Encore Casino 15 miles away.
This 2170 sq ft rental sleeps 4 guests, featuring 2 bedrooms, 1 bathroom, a fully stocked eat-in kitchen with a fridge, microwave, and dishwasher, air conditioning, parking, and a spacious deck for outdoor enjoyment.
Casino Near - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$342/nightfor 1 night

Casino Near

3 2
apartment , Malden
This Malden rental is located 3.8 miles from Cambridge College and 5.2 miles from Inman Square, with Logan Airport 5 miles away.
This 1800 square foot, family-friendly apartment accommodates up to 5 guests with 3 bedrooms, 2 bathrooms, a full kitchen, air conditioning, a private balcony, a sun terrace, and free WiFi and parking.

Choose the Right Vacation Rentals with a Pool in Winthrop, MA

A vacation rental with a pool in Winthrop, MA is the ideal way to complement your daily coastal adventures.

Luxe Everett 2br2ba W/ Pool, Gym & Parking - Winthrop, MA
10 1 review
Winthrop, MA
08/19 – 08/28
$490/nighttotal: $4410 (9 )

Luxe Everett 2br2ba W/ Pool, Gym & Parking

6 2
apartment , Everett
This Everett rental is centrally located, offering a 5-minute drive to TD Garden and a 7-minute drive to the New England Aquarium, with Chelsea Station a 14-minute walk away for regional travel.
This 900-square-foot unit accommodates up to 5 guests with 6 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a swimming pool, garden with barbecue, and on-site billiards.
Family Suite In Boston With Pool Gym & Balcony - Perfect Stay - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$1643/nightfor 1 night

Family Suite In Boston With Pool Gym & Balcony - Perfect Stay

1 2
apartment , Boston
This Boston condo offers a 14-minute walk to the Freedom Trail and is 0.9 miles from Boston Common, placing you near historical sites like the Boston Tea Party Ship & Museum.
This 1190 sq ft residence accommodates 12 guests with 2 bathrooms, featuring a kitchen with a dishwasher and microwave, air conditioning, a fireplace, an outdoor pool, a garden, a fitness center, and parking.
Elegant Oasis With Pool And Gym - Winthrop, MA
10 9 reviews
Winthrop, MA
08/19 – 08/28
$396/nighttotal: $3564 (9 )

Elegant Oasis With Pool And Gym

2 2
apartment , Everett
This Everett apartment rental is conveniently located near Encore Boston Harbor and Assembly Row, a 14-minute walk from Chelsea Station providing easy access to public transportation.
The 1000-square-foot apartment features two bedrooms, one bathroom, accommodates six guests, and includes a private garden, in-unit laundry, and a fully equipped kitchen with modern appliances.
Luxury South End Apartment With Rooftop Pool - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$1284/nightfor 1 night

Luxury South End Apartment With Rooftop Pool

1 2
apartment , Boston
This luxury South End apartment is located a 13-minute walk from Boston South Station and 0.6 miles (approximately 3,168 feet) from Back Bay, offering convenient access to transit and popular neighborhoods.
This 750-square-foot residence accommodates up to 9 guests and features a fully equipped kitchen with a dishwasher, air conditioning, and a rooftop swimming pool with city views, alongside an on-site fitness center.

Top-Rated Oceanfront Vacation Rentals in Winthrop, MA

Relax near the shore in these coastal Winthrop, MA vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.

The Wave: Oceanside Escape - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$1089/nightfor 1 night

The Wave: Oceanside Escape

3 2
houseboat , Boston
Enjoyable 2-bedroom Apartment Near Airport With Washer And Dryer - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$277/nightfor 1 night

Enjoyable 2-bedroom Apartment Near Airport With Washer And Dryer

2 2
apartment , Chelsea
Prime Seaport 2br Steps To Convention Center - Winthrop, MA
Winthrop, MA
09/22 – 09/23
$916/nightfor 1 night

Prime Seaport 2br Steps To Convention Center

2 2
apartment , Boston
Waterfront House Minutes From The Boston Downtown, Airport, Encore Casino - Winthrop, MA
9.5 247 reviews
Winthrop, MA
09/22 – 09/23
$689/nightfor 1 night

Waterfront House Minutes From The Boston Downtown, Airport, Encore Casino

3 2
apartment , Chelsea

Traveler-Approved Luxury Vacation Rentals in Winthrop, MA

Refined interiors and prime locations make these luxury waterfront vacation rentals in Winthrop, MA the ideal choice for your stay.

Pet Friendly Studio | Walk To Mgh - Winthrop, MA
9.2 15 reviews
Winthrop, MA
08/19 – 08/28
$268/nighttotal: $2412 (9 )

Pet Friendly Studio | Walk To Mgh

1 2
apartment , Boston

Explore Vacation Rentals with Saunas in Winthrop, MA

Relax in style with an on-site sauna at these premium Winthrop, MA vacation rentals near the water.

Guest Suite On The Hill - Winthrop, MA
9.9 108 reviews
Winthrop, MA
09/22 – 09/23
$314/nightfor 1 night

Guest Suite On The Hill

1 2
apartment , Boston
©2026 cozycozy.com