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Best Vacation rentals and Airbnb offers in Winthrop, MA
Winthrop, MA
09/22 – 09/23
$409/nightfor 1 night
Modern City & Water View 1-bedroom Apartment With Ac. 4 Blocks From T/ Beach
1 2
apartment , Boston
This East Boston residence offers unobstructed views of the Boston skyline and harbor, with Revere Beach just a short drive away and downtown attractions like TD Garden easily accessible. This 1000-square-foot apartment accommodates up to 4 guests, featuring a king-size Sleep Number bed, a fully equipped kitchen, air conditioning, internet, and a private deck with city and water vistas.
10 8 reviews
Winthrop, MA
09/22 – 09/23
$362/nightfor 1 night
2 Bedroom's 1 Bathroom \N10 Min-airport/downtown Boston \N7 Min-encore Casino
2 2
apartment , Everett
This Everett apartment rental is conveniently located near Encore Boston Harbor (a 4-minute drive) and Assembly Row (a 6-minute drive), offering easy access to major attractions. The two-bedroom, one-bathroom unit sleeps four guests and includes a fully equipped kitchen with appliances (refrigerator, microwave, dishwasher), free Wi-Fi, air conditioning, and on-site parking.
9.1 369 reviews
Winthrop, MA
09/22 – 09/23
$488/nightfor 1 night
Cozy Furnished Studio In Beacon Hill #4
1 2
studio , Boston
This studio apartment is located in Boston's charming Beacon Hill neighborhood, just a short walk from historic landmarks like King's Chapel and Old State House. Guests consistently rate this accommodation as very good for cleanliness, location, and overall experience. This one-bedroom apartment offers 300 square feet of space and comfortably accommodates two guests. The studio features a fully equipped kitchenette, modern amenities like a walk-in shower and hair dryer, and free Wi-Fi for staying connected.
9.4 232 reviews
Winthrop, MA
08/19 – 08/28
$330/nighttotal: $2970 (9 )
Prime Location | Beacon Hill & Financial District
1 2
apartment , Boston
This Boston apartment is located in the heart of downtown, just a short walk from Suffolk University, Quincy Market, Faneuil Hall Marketplace, and Boston Common. The apartment has excellent user, location, and cleanliness ratings. The unit is a one-bedroom, one-bathroom apartment that comfortably sleeps two guests. The apartment includes a fully equipped kitchen, in-unit laundry, air conditioning, parking, and other modern amenities.
10 45 reviews
Winthrop, MA
08/19 – 08/28
$364/nighttotal: $3276 (9 )
North End 1 Br In Little Italy
1 2
apartment , Boston
This North End condo is located one block from Hanover Street, offering easy access to the Boston waterfront and proximity to the Haymarket, North Station, and Aquarium MBTA subway stations. The fully renovated one-bedroom, one-bathroom unit sleeps two guests and features a new kitchen with dishwasher, a 55” 4K Smart TV with Comcast cable, central A/C, a shared roof deck, and includes a complimentary harbor sail (subject to availability and age restrictions).
10 54 reviews
Winthrop, MA
09/22 – 09/23
$455/nightfor 1 night
Casa De Los Clarey Boston Airport Beaches Off Street Parking Available
3 2
apartment , Winthrop Town
This Winthrop Town apartment is just a 6-mile drive from downtown Boston landmarks like Suffolk University, Faneuil Hall Marketplace, and TD Garden, offering a peaceful escape from the city. It's highly rated by guests for its comfort and convenience. The 2-bedroom apartment offers 1190 square feet of space, comfortably accommodating up to 6 guests. Enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, and a private balcony, perfect for relaxing after a day of exploring.
8.2 93 reviews
Winthrop, MA
09/22 – 09/23
$367/nightfor 1 night
Beautiful 2-bedroom, 2-bath Townhouse
2 2
apartment , Boston
This two-bedroom townhouse is conveniently located in Boston, just a short drive from the JFK Presidential Library & Museum, the Boston Museum of Fine Arts, and Boston South Station. Guests have consistently rated the apartment highly for its cleanliness, location, and overall experience. The 1000-square-foot apartment comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, air conditioning, a terrace, a balcony, and free Wi-Fi, ensuring a comfortable and enjoyable stay in Boston.
9.7 306 reviews
Winthrop, MA
08/19 – 08/28
$194/nighttotal: $1746 (9 )
#5 Modern Suite W/ King Bed & Jacuzzi Near Boston
1 2
apartment , Everett
This Everett apartment is conveniently located just a short distance from Boston and Cambridge, making it an ideal base for exploring the area. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The one-bedroom unit can accommodate up to two guests and features a fully equipped kitchen, a luxurious Jacuzzi tub, and a comfortable queen-size bed. Amenities like XFINITY cable TV, high-speed Wi-Fi, a work desk, and a private driveway with a security camera ensure a convenient and secure stay.
9.9 372 reviews
Winthrop, MA
08/19 – 08/28
$252/nighttotal: $2268 (9 )
Cody's Place Winthrop Boston Logan Airport Beaches
1 2
apartment , Winthrop Town
This basement apartment is directly across the street from the Atlantic Ocean and the Winthrop Arms Hotel/Restaurant, offering stunning ocean views and easy access to the beach. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This rental has one bedroom, one bathroom, and a floor area of 360 square feet, comfortably accommodating up to two guests. Enjoy a private entrance, a shared pool and yard, a dedicated parking spot, and complimentary amenities like coffee, water, and access to streaming services.
9.5 49 reviews
Winthrop, MA
09/22 – 09/23
$274/nightfor 1 night
(Mgh9-4) Bright Beacon Hill Studio
1 2
apartment , Boston
This Beacon Hill studio is steps from the Massachusetts State House, Boston Common, and Charles Street shops, offering easy access to the Charles/MGH T-stop and major hospitals. The cozy unit sleeps two, includes a fully equipped kitchen with a fridge, freezer, and microwave, high-speed WiFi, a smart TV, and offers a 10% discount for medical stays or a charitable donation alternative.
9.8 35 reviews
Winthrop, MA
09/22 – 09/23
$350/nightfor 1 night
Serenity - 36’ Aft Cabin Carver
1 2
boat , Boston
Constitution Marina's Bed & Breakfast Afloat is conveniently located in Boston Harbor, just a short walk from the Freedom Trail and other popular attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. This unique floating accommodation offers a master stateroom and a second stateroom with bunks, comfortably accommodating up to four guests. Enjoy modern amenities like air conditioning, Wi-Fi, a kitchen with a refrigerator and microwave, and an outdoor deck with stunning harbor views, perfect for relaxing or working remotely.
9.5 130 reviews
Winthrop, MA
08/19 – 08/28
$156/nighttotal: $1404 (9 )
Home Away From Home Beach,logan,encore, Downtown
1 2
apartment , Revere
This Revere apartment is a short walk from the beach and a fifteen-minute walk from the nearest train station, offering easy access to both the sand and public transportation. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This one-bedroom, one-bathroom rental comfortably sleeps two guests. Amenities include air conditioning, a kitchen with a fridge, freezer, and microwave, and security cameras.
Best Winthrop, MA vacation rentals with a balcony
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.
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.
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.
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.
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.
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.
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.
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?
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
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.
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.
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.
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.
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.
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.
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.
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.
Winthrop, MA
09/22 – 09/23
$1089/nightfor 1 night
The Wave: Oceanside Escape
3 2
houseboat , Boston
Winthrop, MA
09/22 – 09/23
$277/nightfor 1 night
Enjoyable 2-bedroom Apartment Near Airport With Washer And Dryer
2 2
apartment , Chelsea
Winthrop, MA
09/22 – 09/23
$916/nightfor 1 night
Prime Seaport 2br Steps To Convention Center
2 2
apartment , Boston
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.
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.