House vacation rentals in Winthrop

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Top-rated house rentals in Winthrop

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

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Top guest favorite
The great room is highlighted by 25-foot ceilings and panoramic windows offering views of the ocean. A large sectional sofa surrounds a coffee table, while a flat-screen TV is mounted above the fireplace. Sliding glass doors lead to an outdoor space, enhancing the airy feel.
Home in Swampscott
4.91 out of 5 average rating, 111 reviews

Ocean Views at Casa de Mar near Salem & Boston

Relax and unwind at Casa de Mar - our 3 bed, 3 full bath seaside home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, a desk, and 2 seating areas. Modern kitchen, new appliances. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

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
4.77 out of 5 average rating, 218 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.

Top guest favorite
A cozy living area features two comfortable sofas flanking a light wood coffee table, with a decorative plant positioned atop it. A flat-screen television is displayed across from the seating. Large windows allow natural light to illuminate the space, complemented by soft lighting from a nearby lamp.
Home in Tufts University
4.93 out of 5 average rating, 126 reviews

Cozy & Modern 2 Bedroom House - Free Parking !

Welcome to our charming, renovated bungalow near Tufts University has been meticulously cared by owner and is ready to welcome new guests. Enjoy 2 beds/1 bath, private parking, and walkable access to Medford's attractions including; banks, shopping centers, local restaurants/cafes, Encore casino, public transportation, Middlesex Fells Reservation and much more. Tastefully furnished with new queen beds, remote work setup, a relaxing living area, and a fully equipped kitchen for your comfort.

Top guest favorite
A bright sleeping area features a spacious white bed adorned with crisp linens. Natural light enters through sheer curtains, highlighting the wooden flooring and exposed beam ceiling. A small side table holds a lamp, creating a serene environment complemented by indoor plants.
Home in Lakeside Marblehead
4.98 out of 5 average rating, 214 reviews

Authentic Rustic Single Family Home in Old Town

Restored 1800's little single family home. Cozy, clean and artistically renovated to retain authenticity. Located in Old Town - walk to everything! Back yard patio with BBQ, perfect for morning coffee. Off street Parking! 4.6 miles to salem witch museum. Boston is 19 miles. Starbucks is a 2 minute WALK. Explore our little town and fall in love. Please this is not a party house. It is in a tiny little neighborhood. Quiet time 10pm - 8am. I want my precious home back in clean condition. Thx

Superhost
The living room features a comfortable couch adorned with a soft throw blanket. A large piece of artwork hangs on the wall, showcasing a vibrant floral design. Two stylish glass tables are positioned in front of the couch, accompanied by a decorative rug.
Home in Hyde Park
4.9 out of 5 average rating, 355 reviews

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

Top guest favorite
A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.
Home in Stoneham
4.92 out of 5 average rating, 293 reviews

Entire Apartment in Stoneham

Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

Guest favorite
A modern kitchen features sleek white cabinets and stainless steel appliances. A spacious island with a cooktop is surrounded by red metal stools. Natural light fills the area through a nearby window, complementing the contemporary design and providing a warm, inviting atmosphere.
Home in South Boston
4.92 out of 5 average rating, 420 reviews

3 BR Private Family Home, S. Boston/Seaport/BCEC

A beautiful single home all to yourself with a private entrance AND GARAGE PARKING in bustling South Boston! Equipped with 3 private bedrooms as well as two bathrooms and outdoor deck space that opens to a small park, this home features plenty of amenities in an unbeatable location with access to a plethora of shops and restaurants. One mile exactly to the Convention Center (BCEC).This is the perfect place for large groups and companies who seek a quiet comfortable Boston experience.

Top guest favorite
A spacious bedroom is illuminated by natural light from large windows, featuring a comfortable bed with soft linens. Two plush armchairs are positioned across from a cozy sofa. A modern glass coffee table holds a magazine, while decorative elements add charm to the setting.
Home in Cambridge
4.94 out of 5 average rating, 301 reviews

Stunning urban hideaway nearby Harvard Square

Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

Top guest favorite
Home in Malden
4.93 out of 5 average rating, 167 reviews

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

Guest favorite
A charming outdoor seating area is framed by a white fence and vibrant greenery. Comfortable seating is arranged around a low table, with bright orange cushions adding a lively touch. Potted plants with colorful flowers complement the inviting space, creating a pleasant atmosphere.
Home in Everett
4.93 out of 5 average rating, 378 reviews

Prime location near Boston

Home in Everett, MA. Located just a 20 minute walk from Encore Boston Harbor Casino. This location is also just a 15 minute drive from downtown Boston. Room in the basement has a microwave, refrigerator, coffee maker, and hot water for making tea which is provided along with light snacks and coffee. There is a desk for laptop. Queen Tempurpedic Mattress topper as well as a pull out sofa. Private bathroom with spacious shower. See guide book for more info on the area!

Superhost
A spacious bedroom is shown, featuring a black bed with a textured bedding set displaying ocean waves. A cozy armchair sits beside a radiator, and a small folding table is placed nearby. Natural light enters through a window with patterned curtains.
Home in Chelsea
4.83 out of 5 average rating, 403 reviews

10 minutes to Airport-Boston-Casino (2G)

(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.

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, 286 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.

Popular amenities for Winthrop house rentals

When is the best time to visit Winthrop?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$17,549 GYDG$20,056 GYDG$20,474 GYDG$25,070 GYDG$26,533 GYDG$28,622 GYDG$27,369 GYDG$27,786 GYDG$22,563 GYDG$22,772 GYDG$21,101 GYDG$21,937 GYD
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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 G$8,357 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,170 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

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