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Apartment holiday rentals in Winthrop

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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 $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 5,380 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 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

    90 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

Top-rated apartment rentals in Winthrop

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

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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.
Apartment in Winthrop

Grand 2BR Sleeps 6 • Boston • Airport & Beaches

Whether you’re traveling for work or vacation, solo, as a couple, with friends or family, this spacious, sun-filled 7-room apartment is the perfect home base. Comfortably sleeps up to 6 guests with 2 bedrooms, a full kitchen, living room, dining room, sunroom, 2 private porches, free off-street parking, oak hardwood floors, original gumwood trim, and on-site coin laundry. Minutes from Logan Airport, public transportation, beautiful Winthrop and North Shore beaches, and Boston’s top attractions.

4.87 out of 5 average rating, 266 reviews
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

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.

4.96 out of 5 average rating, 285 reviews
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.
Apartment in Revere

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.

4.92 out of 5 average rating, 261 reviews
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.
Apartment in East Boston

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.

4.75 out of 5 average rating, 170 reviews
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.
Apartment in Nahant

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.

4.95 out of 5 average rating, 182 reviews
Top 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.
Apartment in Revere

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.

4.96 out of 5 average rating, 164 reviews
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 Revere

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.

4.88 out of 5 average rating, 249 reviews
Guest favourite
A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.
Apartment in Winthrop

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to 8 guests, making it perfect for families or groups of friends. Located on the 2nd floor of a historic building, this home offers a bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area, kitchen and private deck with ocean views.

4.84 out of 5 average rating, 133 reviews
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.
Apartment in Lynn

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

4.94 out of 5 average rating, 232 reviews
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 Revere

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.

4.95 out of 5 average rating, 151 reviews
Top Guest favourite
The exterior of a stylish two-family home is depicted, featuring a welcoming porch with white railings and a neatly landscaped front yard. Flowering plants, small trees, and a paved pathway lead to the entrance. The upper floor includes strategically placed windows, allowing natural light to filter in.
Apartment in Winthrop

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

4.96 out of 5 average rating, 118 reviews
Top Guest favourite
A spacious porch offers a tranquil ocean view, featuring a circular table surrounded by comfortable chairs. The sun sets over the water, casting warm hues across the scene, while trees frame the area, enhancing the inviting outdoor space.
Apartment in Revere

Ikram's Place Close to Boston,Subway,Airport,Beach

Our place is located in North of Boston, in a very quite neighborhood , it has a Great Ocean view, free parking in the property, front yard and back yard. We offer coffee, milk, Tea, toast, bottled of water, OJ,eggs, etc. 1 min walking to the Beach,7 min to the T and 10 min to Downtown Boston via subway. total Privacy in the whole apartment .Our place is good for couples, solo adventurers, business travelers, and families.

4.96 out of 5 average rating, 225 reviews

Popular amenities for Winthrop apartment rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

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 Revere

Beachmont Guest Suite

4.94 out of 5 average rating, 211 reviews
Guest favourite
Apartment in Revere

Boston 3 Room Apt 5 Min Walk to Train & Beach

4.91 out of 5 average rating, 349 reviews
Top Guest favourite
A spacious living area features a high wood-beamed ceiling and large windows overlooking greenery. A comfortable couch and plush chairs are arranged around a coffee table. A staircase leads to a loft area, and a flat-screen TV is visible in the background.
Apartment in Roxbury

Light-Filled Luxury Apartment with View

4.97 out of 5 average rating, 436 reviews
Guest favourite
A spacious window with dual openings frames a view of the ocean and sandy beach across the street. The interior walls are painted in a calming blue, complementing the natural light that fills the room. Grassy areas can be seen in the foreground.
Apartment in Nahant

The Blue Pearl

4.97 out of 5 average rating, 119 reviews
Guest favourite
Apartment in Medford

Hipster Basecamp | Fireplace • Deck • Parking

4.98 out of 5 average rating, 314 reviews
Top Guest favourite
A modern kitchen is highlighted with white cabinetry and stainless steel appliances. A round wooden table with four upholstered chairs is positioned near the center, set with placemats. Bright overhead lighting enhances the open layout, revealing a view of additional kitchen features.
Apartment in Somerville

Lovely apt near Boston/Assembly Row/Encore Casino

4.97 out of 5 average rating, 113 reviews
Top Guest favourite
Apartment in Woburn

Newly Finished Guest Haven in Woburn

4.89 out of 5 average rating, 170 reviews
Guest favourite
A living room is featured with hardwood floors and exposed brick walls, creating a cozy ambiance. A large TV sits atop a white media console. A comfortable blue chair with a patterned cushion provides seating, while a coffee table enhances the space. Artwork decorates the walls.
Apartment in Chelsea

Convenient Cozy Clean Public Trans Free parking

4.94 out of 5 average rating, 437 reviews

Private apartment rentals

Top Guest favourite
A living area features a gray sectional sofa paired with a blue accent chair. A white coffee table is positioned in front of the sofa. A television mounted on the wall displays various streaming options, while natural light filters through a nearby window.
Apartment in Salem

Instant Book/Parking/Wk + Mo Discounts

4.91 out of 5 average rating, 198 reviews
Top Guest favourite
A ground floor entrance is framed by a white door with a glass panel, set against a backdrop of light-colored siding and brick. Potted plants and landscaped borders add greenery, with a paved pathway leading to the door.
Apartment in Salem

Your home for the holidays!

4.96 out of 5 average rating, 979 reviews
Guest favourite
A comfortable living area features a brown sofa adorned with decorative pillows. A black coffee table sits in front, with a bouquet of flowers on top. A table for dining is positioned near the window, with sunlight streaming in, illuminating the kitchen's wooden cabinets and appliances.
Apartment in East Boston

*Boston*Arprt*TD*FreedomTrail*ConvCtr*Fnway*T*MGH*

4.76 out of 5 average rating, 1028 reviews
Guest favourite
A comfortable living area is showcased, featuring a brown leather sofa and a wooden coffee table. A glass dining table with two chairs is positioned nearby. A flat-screen TV is mounted on a wall, with a kitchen area visible in the background.
Apartment in Dorchester

1 bed, 2 rooms, 4 guests Cute&new. Free parking

4.94 out of 5 average rating, 206 reviews
Guest favourite
Apartment in Winthrop

Beach Bungalow

4.93 out of 5 average rating, 44 reviews
Guest favourite
A view from the property showcases the oceanfront road, lined with low greenery and distant buildings along the shore. The ocean extends toward the horizon under a partly cloudy sky, providing a serene coastal atmosphere.
Apartment in Winthrop

Oceanfront apartment, 15min from Boston!

4.88 out of 5 average rating, 90 reviews
Top Guest favourite
Apartment in Winthrop

Ocean View Beachfront | Near Boston | Free Parking

4.98 out of 5 average rating, 56 reviews
Top Guest favourite
An open living area features warm wood floors and neutral-colored walls. A large dining table is surrounded by white chairs, with a light fixture above. A television is mounted on the wall opposite a comfortable sofa, complemented by a decorative plant and a textured area rug.
Apartment in Winthrop

Charming condo steps from beach

4.94 out of 5 average rating, 79 reviews

Apartment rentals with a hot tub

Guest favourite
Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

4.93 out of 5 average rating, 242 reviews
Top Guest favourite
Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

4.98 out of 5 average rating, 221 reviews
Guest favourite
The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.
Apartment in Roxbury

Modern, Spacious 1BR for 4 - Easy Marathon Access!

4.78 out of 5 average rating, 359 reviews
Guest favourite
Apartment in Somerville

New luxury 4BR/3 bath apt w/AC & EV charger

4.9 out of 5 average rating, 21 reviews
Superhost
Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

4.89 out of 5 average rating, 35 reviews
Top Guest favourite
A living area is presented with a blue futon, complemented by striped pillows. Two bright orange chairs are positioned beside a small black table. A light fixture with an arc design hangs above, illuminating the space. A door leads to an adjacent room.
Apartment in North End

Amazing Location in Little Italy with Roof Deck

5.0 out of 5 average rating, 88 reviews
Top Guest favourite
Apartment in Salem

Historic home on Salem Neck

4.95 out of 5 average rating, 22 reviews
Superhost
Apartment in South End

Brand-new over Tatte Bakery, pool + prime location

New place to stay

When is the best time to visit Winthrop?

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Avg. price$253 NZD$241 NZD$271 NZD$307 NZD$334 NZD$388 NZD$349 NZD$353 NZD$328 NZD$349 NZD$285 NZD$252 NZD
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