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Apartment holiday rentals in Winthrop

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Winthrop

Guests agree: These apartments are highly rated for location, cleanliness and more.

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Guest favourite
A spacious sleeping area features a bed with a neutral white bedspread. Bedside tables with lamps are positioned on either side of the bed. Natural light filters through sheer curtains, illuminating the hardwood floors and an area rug with a subtle pattern.
Apartment in East Boston
4.75 out of 5 average rating, 138 reviews

Studio in East Boston #1

Peaceful and comfortable studio located in East Boston, Ma! It is located 10 mins away from the airport and 15 away from downtown Boston. It is also a 2 min walk from the train station. Guest will have full access to this studio which offers a bedroom, bathroom and kitchen area. Airport train station (10 mins), free shuttles to terminals. Kids under 3 years old don’t count as a guest. We offer a pack n play with a mattress! There is NO SMOKING inside the apt or hallways, fine will be charged.

Top Guest favourite
A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.
Apartment in Winthrop
4.96 out of 5 average rating, 265 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Top Guest favourite
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Apartment in Ashmont
4.96 out of 5 average rating, 146 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Superhost
The exterior of a two-story blue house is presented, featuring a brick facade and multiple windows. A covered porch with stairs leads to the entrance, surrounded by neatly trimmed shrubs. Sunlight illuminates the scene, highlighting the clear blue sky.
Apartment in Winthrop
4.75 out of 5 average rating, 194 reviews

The Price is Right Boston Airport Beach Park Free

Private spacious 1 bed 1 bath 3rd Fl Attic Apt. Great place to rest your head or use as a base to Boston, The Encore Casino, Salem & beyond! Subtle skyline view of Boston in a beautiful safe quiet residential neighborhood. New Rug/Paint/AC Comfy Queen Mattress 55” Smart TV blackout shade ceiling fan nightstands lamps 2 chairs Living Areas New Comfortable long 89” Couch 2 Tables/Chairs/Lamps Kitchenette full size Fridge Freezer Microwave Keurig Air Fryer comboToaster Oven Electric Kettle

Guest favourite
A spacious living area with a plush sectional couch in a neutral tone, centered around a coffee table, invites relaxation. Large sliding glass doors frame panoramic ocean views and provide natural light. A modern gas fireplace and stylish decor enhance the cozy atmosphere.
Apartment in Beachmont
4.96 out of 5 average rating, 178 reviews

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

Top Guest favourite
A modern living area features a light gray sectional sofa complemented by a round gray ottoman and a blue accent chair. Framed artwork is displayed above the sofa, with a vibrant blue wall enhancing the space. A television is mounted on one wall, and large windows allow natural light.
Apartment in East Boston
4.92 out of 5 average rating, 105 reviews

Chic Condo near T Station & Airport.

Welcome to our brand new, luxurious apartment. Conveniently located just two T stops away from Logan Airport and 2min walking distance from Orient Heights T station, Constitution Beach and just 12min to downtown. You'll have easy access to explore the city's top attractions including Fenway Park, Boston’s theater district, Beacon Hill, Harvard and MIT universities, the Aquarium, Quincy Market, museums, public garden, ducklings and swan boats, Newbury Street and even Salem MA (Witch City).

Top Guest favourite
The spacious living room features hardwood floors with an orange accent wall and contemporary artwork. A comfortable sofa and decorative throw blankets are arranged around a coffee table adorned with seasonal decor. A faux fireplace adds a decorative touch, while a small bench provides additional seating.
Apartment in Beachmont
4.89 out of 5 average rating, 229 reviews

Stunning Oceanview-4 Train Stop Logan Airport

Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

Top Guest favourite
The kitchen showcases dark wood cabinetry paired with granite countertops, featuring a stainless steel refrigerator and oven. A mosaic backsplash adds a touch of color, while a table with a floral tablecloth provides a casual dining space. Natural light floods the area through the window.
Apartment in Revere
4.89 out of 5 average rating, 531 reviews

-2 Traditional 3 BR/2 Bath/Prkng By Arprt/Bos

Our 2nd floor condo is close to the airport and was gutted and totally rebuilt with high-end finishes. There is plenty of space for guests in your group to sit, relax, and mingle. There is a kitchen. a formal dining room, a master BR with en suite bathroom, 2 more BRs and a 2nd bath. Please specify the number of guests in your group when booking. Access and rate depend on the number of guests. See our other listings https://www.airbnb.com/h/reveregem1 https://www.airbnb.com/h/reveregem

Top Guest favourite
A modern living area showcases a grey sectional sofa, complemented by a geometric area rug. A small coffee table sits in front, and a desk with a chair is positioned nearby. Large windows provide natural light, and a cityscape photograph adorns the wall.
Apartment in East Boston
4.88 out of 5 average rating, 120 reviews

1 BR Gem 5min to Train & Airport explore the city

This modern stylish place to stay is perfect to explore the city of Boston. It’s a hidden gem 1 block away from the Blue Line T station, two stops away from downtown, the aquarium, TD Garden, Faneuil Hall, and multiple museums. 2 mins walking distance from the apartment to Piers Park and spectacular views of Boston Harbor and the skyline.Hop on the ferry to explore Seaport restaurants and bars close by with differing cultures and cuisines. Only 2 min from Logan Airport via train or car.

Top Guest favourite
The living room features two sofas, one in a solid color and the other with a striped pattern, facing a large window that offers ocean views. A light-colored area rug lies on the wooden floor, and a simple coffee table is centered in the space.
Apartment in Beachmont
4.95 out of 5 average rating, 125 reviews

2 Bedroom Apartment with Ocean Views

Quiet, newly renovated 2 bedroom apartment just outside Boston 180 degree ocean views 10-15 min walk to subway with quick access to Goverment Center, MGH, Aquarium, North End and TD Garden. Beach access accross the street and short walk to Revere Beach. Lots of good resturaunts and cafes nearby. Unit is located on the 3rd floor. 3 sets of stairs to access apartment. Perfectly safe but not handicap accessible or convenient for anyone with impaired mobility or small children.

Guest favourite
A bright studio space features a spacious bed with a light-colored blanket. Decorative wall art hangs above the bed, while a cozy seating area with a gray sofa and a coffee table is visible in the background. Natural light streams through nearby windows.
Apartment in Revere
4.92 out of 5 average rating, 197 reviews

Corner Cottage - cozy studio just north of Boston

Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

Guest favourite
A modern living area features a sectional sofa with a textured blue fabric, positioned on a patterned rug. A bright kitchen is visible in the background, showcasing wooden cabinetry and stainless steel appliances, while large windows allow natural light and views of the outdoors.
Apartment in Beachmont
4.81 out of 5 average rating, 122 reviews

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,

Discover comfort and style in our 2-bed, 2-bath apartment. Modern decor, fully equipped kitchen, and cozy bedrooms await. Enjoy the convenience of nearby attractions, like Revere Beach and downtown Boston. Parking onsite is free. Your home away from home for a memorable Boston experience! The two bedrooms are thoughtfully designed to ensure a restful night's sleep. Both bedrooms are equipped with King sized beds. You will have the apartment all to yourself.

Popular amenities for Winthrop apartment rentals

When is the best time to visit Winthrop?

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Avg. price$192 AUD$215 AUD$244 AUD$247 AUD$293 AUD$266 AUD$296 AUD$299 AUD$278 AUD$286 AUD$225 AUD$213 AUD
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Quick stats about apartment rentals in Winthrop

  • Total holiday rentals

    Explore 90 holiday rentals in Winthrop

  • Nightly prices starting at

    Winthrop holiday rentals start at $74 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,260 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Winthrop holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Winthrop rentals

  • 4.8 Average rating

    Winthrop stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Winthrop's top spots, include Orient Heights Station, Beachmont Station, and Suffolk Downs Station