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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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Top guest favourite
The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.
Flat in Winthrop
4.97 out of 5 average rating, 339 reviews

World Cup Boston • Pool • Sleeps 4 • Near Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

Guest favourite
Flat in Revere
4.91 out of 5 average rating, 330 reviews

Boston 3 Room Apt 5 Min Walk to Train & Beach

Sunny 1st floor 3 room apartment with private entrance, in a 150 year old historic home. A short walk to Revere Beach and a 10 minute walk to the MBTA Blue Line, be at Logan Airport or Downtown Boston in minutes. Historic Salem is just a short ride and available by pubic transportation The apartment has a full kitchen, spacious bedroom with very comfortable king size bed, recliner and TV. The living room has a leather sofa, comfy twin size daybed and TV. Laundry on site. Free Driveway Parking.

Top guest favourite
An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.
Flat in South Boston
4.99 out of 5 average rating, 121 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Superhost
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.
Flat in East Boston
4.75 out of 5 average rating, 157 reviews

Studio in E. 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.
Flat in Winthrop
4.96 out of 5 average rating, 271 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.

Guest favourite
A light-filled corner of the living area features a sectional sofa in soft gray, complemented by a small coffee table. Three windows dressed in blinds allow natural light to filter in, enhancing the cozy and inviting atmosphere.
Flat in Revere
4.92 out of 5 average rating, 250 reviews

Quiet Neighborhood Luxury Stay

The apartment is brand new with a modern feel to it. Available with all the amenities needed for your convenience. Very quiet, clean, and safe neighborhood. Close to everything you desire, 1 minute to the beach, 8 minutes away from the train station, 1 minute away from the T-Bus stop, 9 minutes to Logan Airport, 12 minutes to Downtown Boston, 15 minutes away from Encore Casino, food and coffee shops, such as Starbucks and Dunkin' Donuts in the area. Perfect for a family stay or a business trip.

Top guest favourite
A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.
Flat in Nahant
4.95 out of 5 average rating, 166 reviews

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

Guest favourite
A spacious bedroom features a large bed dressed in white sheets and a light blue blanket. Nightstands with lamps are positioned on either side of the bed. A subtle area rug adds warmth, while a painting hangs on the wall, complementing the calm color scheme.
Flat in Revere
4.96 out of 5 average rating, 156 reviews

Spacious 3 Bedroom Apartment with King Bed

Family friendly, walk-out basement style apartment close to everything! Clean and safe neighborhood. A 10 minute walk to two beaches: Revere Beach - America's first public beach & Short Beach - a neighborhood favorite. 5 minute walk to Beachmont T station and bus lines - 15 minutes to Downtown Boston! 10 minute drive to Logan or 20 minute drive to the Casino. 25 minute drive to Salem. Walkable to an Italian Bakery, Dunkin Donuts and Starbucks as well as a number of restaurants and eateries.

Superhost
The dining area features a wooden table surrounded by six blue chairs, complemented by a cozy couch visible in the background. A full kitchen is equipped with a refrigerator, stove, and ample counter space. Natural light brightens the space through large windows.
Flat in East Boston
4.87 out of 5 average rating, 131 reviews

2bd Apt, 3 min walk to train, 7min to airport

Peaceful, private, comfortable and recently renovated 1st floor apartment. Located 3 minutes walk from Suffolk Downs train station and 1 PARKING SPACE. Furnished with all amenities including washer, dryer, wifi, 3 tvs, full kitchen. Conveniently close to downtown Boston. You will love this spacious apartment located in East Boston. 18 minutes by train to Government Center/Downtown Boston. 15 minutes to Faneuil Hall/ Quincy Market and 7 minutes to Revere Beach by public transportation.

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.
Flat in Revere
4.89 out of 5 average rating, 238 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
An air hockey table is centered in a bright, modern room. The table's glossy surface features distinct markings for gameplay. To the side, a simple plant and a decorative white vase complement the clean aesthetic of the space.
Flat in Lynn
4.93 out of 5 average rating, 206 reviews

Modern & Cozy Apt close to Boston and Salem

New & Modern, Close to the beach , 15 minutes to the airport & BOSTON. Close to the beach, Salem, & Boston. minutes away from the commuter rail 5 People can comfortably stay here. minutes away from the commuter rail 10 minutes away from Salem 15 minutes to the Airport Several basic amenities included like snacks, water, mouthwash, toothbrushes, toothpastes, etc. Washing and Drying machine are included in the stay. Free Parking (Private Driveway) Smart TV with Netflix access included

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.
Flat in Revere
4.96 out of 5 average rating, 135 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.

Popular amenities for Winthrop apartment rentals

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Quick stats about flat rentals in Winthrop

  • Total holiday rentals

    Explore 90 holiday rentals in Winthrop

  • Nightly prices starting at

    Winthrop holiday rentals start at £38 per night before taxes and fees

  • Verified guest reviews

    Over 5,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    90 of Winthrop holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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

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