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Apartment holiday rentals in Winthrop

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Top-rated apartment rentals in Winthrop

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

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Guest favourite
Flat in Beachmont
4.91 out of 5 average rating, 321 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.

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, 149 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.
Flat in Winthrop
4.96 out of 5 average rating, 269 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 Beachmont
4.92 out of 5 average rating, 245 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.

Guest favourite
The image displays a cozy dining area with a glass-topped table surrounded by four chairs. Natural light filters through the windows, highlighting oak hardwood floors and intricate wood trim. An inviting living space is visible in the background, featuring a plush seating arrangement.
Flat in Winthrop
4.87 out of 5 average rating, 260 reviews

Boston World Cup Sleeps 6 Free Parking Near Logan

Perfect for groups visiting for World Cup or exploring the city. This gorgeous, spacious, sun-filled private 7 room apartment sleeps 6 guests & includes free off-street parking, a rare convenience near Boston & Logan Airport. Beautiful oak hardwood floors, original gumwood trim, & classic wainscoting highlight the home’s character. 2 bedrooms full kitchen living room dining room sunroom office & coin-op washer/dryer. Close to public transportation Great 4 groups • 3 porches • Minutes to Boston

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
4.94 out of 5 average rating, 160 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 Beachmont
4.96 out of 5 average rating, 154 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.

Top guest favourite
Flat in Woburn
4.95 out of 5 average rating, 227 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

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.
Flat in Beachmont
4.95 out of 5 average rating, 191 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
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 Beachmont
4.89 out of 5 average rating, 234 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 exterior of the 1850s home is showcased, featuring a modernized grey facade with white trim. A tree stands nearby, casting shadows on the manicured lawn. Brick pathways lead to the entrance, where a welcoming dog is seen in the foreground.
Flat in Salem
4.97 out of 5 average rating, 417 reviews

The Salem House Too

An 1850’s built home with a modern interior and revitalized exterior. It’s the perfect spot to relax and unwind or take work on the road. Located one mile from downtown Salem and away from the traffic, our goal is to provide a classy, upscale experience with all of the comforts of home. Pair a sparkling clean private space with off street parking, unlimited coffee, and a fridge stocked with drinks and snacks and you’ve got The Salem House! Come stay with us and see what Salem is all about!

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 Beachmont
4.95 out of 5 average rating, 130 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

When is the best time to visit Winthrop?

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Avg. price$186 SGD$177 SGD$198 SGD$214 SGD$254 SGD$230 SGD$256 SGD$259 SGD$241 SGD$256 SGD$209 SGD$184 SGD
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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 $64 SGD 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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