House vacation rentals in Winthrop

Find and book unique houses on Airbnb

Top-rated house rentals in Winthrop

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

%{current} / %{total}1 / 1
Top guest favorite
The living area features a dark blue sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front, surrounded by natural light from nearby windows. The white walls and sleek countertops contribute to a modern, open space. A minisplit unit is visible for climate control.
Home in Lakeside Marblehead
5 out of 5 average rating, 152 reviews

Seaside Cottage

Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

Top guest favorite
A dining area is presented with a rustic wooden table surrounded by white chairs. Lush green plants are displayed throughout the space, enhancing its natural light. A geometric pendant light hangs above, while large windows provide views of the bright, open living area beyond.
Home in Medford
4.99 out of 5 average rating, 113 reviews

Family Friendly Green Oasis Minutes from Boston

Oasis filled with natural light, plants & art in a quiet neighborhood minutes from Downtown Boston. Perfect for sightseeing & enjoying the best of the city and neighboring towns. Walk to Wrights Pond for a swim & hike the Middlesex Fellsway Reservation. Fully equipped chefs kitchen. Private backyard surrounded by trees. Wake up to birds chirping and relax after a long day of exploring while you watch your favorite TV show. Enjoy a bath in the soak-in tub. 3 parking spaces, office setup & laundry

Top guest favorite
A cozy living area features a green-tiled fireplace framed by two botanical prints. A wooden bench table with a dark finish is positioned nearby, enhancing the cottage's retro charm. Accent chairs and a patterned rug complete the warm, inviting space.
Home in Hull
4.96 out of 5 average rating, 137 reviews

Retro New England cottage - walk to the beach!

A peaceful beach retreat close to all the action. This one-bedroom bungalow is one of the oldest in the neighborhood and is full of retro charm. The house is within walking distance of Nantasket Beach and is set back from the road in a large, quiet yard. The driveway is big enough to park two cars, so you'll never have to worry about beach parking. Enjoy all Hull has to offer, from fresh seafood to nature reserves and paddleboarding. Convenient ferry access makes a day trip to Boston a breeze.

Superhost
A welcoming living area features a light-colored sofa, a coffee table, and a decorative area rug in soft hues. Natural light enters through the windows, and a door leads outside. A dining area is visible in the background, with a wooden table and chairs.
Home in Hull
4.81 out of 5 average rating, 180 reviews

Homey getaway by the beach

Cute and homey well furnished 3 bedroom apartment in an older 2 family beach house. 1 min walk away from the best and least crowded part of Nantasket Beach, and a short 5 min drive from the Hull downtown. Ideal for vacationers, visitors, and families, the house features 3 bedrooms, 2 full baths, a nice and well equip kitchen with quality Samsung appliances, and a small BBQ deck overlooking a private backyard with a picnic table and stone patio. The house is literally 175 Yards from the beach :-)

Top guest favorite
An open eat-in kitchen features sleek white cabinets and a dark countertop. The kitchen island, which seats three on mint green stools, is set with dishware. Natural light filters through the window shades, complementing the modern appliances and warm color tones.
Home in Everett
4.97 out of 5 average rating, 136 reviews

Gorgeous Retreat - Amazing Kitchen - Hosts 6

PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino Whether you travel for outdoor adventure, beach time, family bonding or just hanging out, this gorgeous two-bedroom home – just minutes away from the beach and Encore Casino and less than 20 minutes from the city center – was lovingly renovated and outfitted to curate an experience of being at home, at peace, and surrounded with quiet beauty. Restaurants, Grocery Store, Pharmacy and other conveniences within minutes walk.

Guest favorite
A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.
Home in East Boston
4.78 out of 5 average rating, 224 reviews

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Guest favorite
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.
Home in Winthrop
4.83 out of 5 average rating, 107 reviews

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 six guests, making it perfect for families or groups of friends. 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 offers ample seating, and the fully equipped kitchen, private deck with breathtaking views of the ocean.

Top guest favorite
The living room features a crimson couch paired with patterned armchairs, arranged around a central coffee table. The space is enhanced by natural light from large windows with shutters. Decorative plants are positioned nearby, contributing to a cozy and welcoming environment.
Home in East Boston
4.98 out of 5 average rating, 198 reviews

Boston Best with Parking - GREAT reviews

**READ our reviews :) - 10min walk to Airport Blue line subway T-stop - 10min drive to Downtown Boston - Local dining options in walking distance - 1 parking spot available upon request - Spacious and comfortable house Welcome to your Best Boston experience. I am Rafael and I will ensure that you get any attention needed with a text, call, or email. We hope that you enjoy our recommendations for activities and meals - we based them on our lifelong East Boston experiences.

Top guest favorite
A large tree with a broad canopy dominates the lush backyard, surrounded by greenery. The area features a stone border outlining a patch of grass, with glimpses of the landscape beyond, including wooded areas and a play structure in the distance.
Home in Danvers
4.98 out of 5 average rating, 117 reviews

Large, Comfortable & Conveniently located Home

You will be close to everything when you stay at this centrally-located private, updated historical home. 4 bedrooms & 2 baths w/plenty of extra space for large families or groups. Fenced-in spacious patio with huge backyard. Sizable, private parking area. Near Routes 95 & 128. Only 25 mins to Boston. Perfect for trips to picturesque points, including Boston, Gloucester, Newburyport, Rockport, Cape Ann, historic Salem & Maine coastal towns and cities. Dog friendly.

Guest favorite
A cozy living area features a beige sofa, a green armchair, and a wooden coffee table with decorative centerpieces. A stylish rug adds texture to the floor. Walls are adorned with artwork and decorative pieces, while natural light filters through the windows.
Home in Lynn
4.91 out of 5 average rating, 289 reviews

Clean, spacious In-Law Suite -Near Everything

Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

Top guest favorite
Home in Swampscott
4.92 out of 5 average rating, 106 reviews

By the Ocean - Egg Rock House - 4 bed 4.5 bath

🐚 Welcome to Egg Rock House - “Wicked awesome” oceanfront home on the scenic shores of New England. Steps to restaurants, shops, nightlife, trains, and endless outdoor fun. Perfect launchpad for visiting Ipswich, Newburyport, Salem, Marblehead, Gloucester, and Rockport. Only 30 minutes by train to Boston’s North Station. Relax on the front deck with sweeping ocean views just outside your door.

Top guest favorite
A spacious living area showcases a modern leather sofa facing a wall-mounted television. Natural light filters through large windows, creating a bright atmosphere. A dining table with light-colored chairs is positioned nearby, with a decorative plant placed in the center.
Home in Lakeside Marblehead
4.98 out of 5 average rating, 157 reviews

Walk To Everything

NOTE FOR WORLD CUP 2026 TRAVELERS: Please be advised this property is not near Foxborough, MA. Roughly 1 1/2-2hrs by car. Much longer by public transportation. Steps from the harbor and minutes to the beach, this modern two-bedroom home has been completely renovated. Free parking on site and surrounded by shopping, food, and more--walking distance to everything you need.

Popular amenities for Winthrop house rentals

When is the best time to visit Winthrop?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ308ﺩ.ﺇ353ﺩ.ﺇ360ﺩ.ﺇ441ﺩ.ﺇ466ﺩ.ﺇ503ﺩ.ﺇ481ﺩ.ﺇ488ﺩ.ﺇ397ﺩ.ﺇ419ﺩ.ﺇ375ﺩ.ﺇ356
Avg. temp-1°C0°C4°C9°C15°C20°C23°C23°C19°C13°C7°C2°C

Quick stats about house rentals in Winthrop

  • Total vacation rentals

    Explore 60 vacation rentals in Winthrop

  • Nightly prices starting at

    Winthrop vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 5,950 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Winthrop vacation rentals include wi-fi 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

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Winthrop
  6. House rentals