Vacation rentals in Winthrop

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Top-rated vacation rentals in Winthrop

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

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Top guest favorite
A spacious outdoor area features a crystal-clear pool surrounded by a paved deck. Several lounge chairs are positioned nearby for relaxation. The house in the background displays a welcoming design with a cozy porch. Lush greenery provides a serene backdrop to this inviting space.
Apartment in Winthrop
4.97 out of 5 average rating, 333 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite
A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.
Guest suite in Winthrop
4.92 out of 5 average rating, 1,356 reviews

Licensed Boston airport studio 5 stars, subway

We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

Top guest favorite
The outdoor area features a serene saltwater pool surrounded by lounge chairs, all set against a backdrop of panoramic ocean views. A pergola provides partial shade, and vibrant flowers add a touch of color to the landscaped surroundings.
Apartment in Winthrop
4.96 out of 5 average rating, 265 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.

Top guest favorite
Condo in Winthrop
4.99 out of 5 average rating, 216 reviews

Truly Oceanfront! Spacious Family Petfriendly Home

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Guest favorite
A private outdoor deck showcases stunning ocean views, furnished with two comfortable chairs facing the water. The serene coastal scenery is framed by a well-maintained railing, creating an inviting space for relaxation. Soft overhead lighting allows for use during the evening.
Apartment in Beachmont
4.96 out of 5 average rating, 180 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 favorite
Apartment in Beachmont
4.89 out of 5 average rating, 230 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.

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 spacious lobby area is highlighted with modern furnishings, including a large, leather sofa and minimalist armchairs. Natural light floods through expansive windows, complemented by greenery from potted plants. The design features a neutral color palette with subtle decorative elements on the walls.
Apartment in Beachmont
4.84 out of 5 average rating, 224 reviews

Stylish and Cozy at Revere Beach

Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Guest favorite
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop
4.95 out of 5 average rating, 1,001 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Superhost
Guest suite in Winthrop
4.83 out of 5 average rating, 139 reviews

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

Top guest favorite
Barn in Nahant
5 out of 5 average rating, 162 reviews

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, fully furnished, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. Parking on premises. The ideal location for a short getaway with family or friends or to unwind after a long day at work. Only 25' from downtown Boston and other North Shore towns with restaurants and bars.

Guest favorite
Apartment in Beachmont
4.91 out of 5 average rating, 319 reviews

Boston 3 Room Apt 5 Min Walk to Train & Beach

Sunny 3 room apartment with private entrance, in 150 year old renovated home. A short walk to Revere Beach and the MBTA Blue Line, be at Logan Airport or Downtown Boston in minutes. The apartment has a full kitchen, spacious bedroom with very comfortable king size bed and TV. The living room has a leather sofa, recliner, desk and TV. Laundry on site. Free Driveway Parking.

Popular amenities for Winthrop vacation rentals

When is the best time to visit Winthrop?

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Frequently Asked Questions

  • Where should I stay in Winthrop?

    Make yourself at home in Winthrop by choosing from our most frequently booked neighborhoods. We have over 200 vacation rentals in Point Shirley, over 2,670 vacation rentals in Orient Heights, and over 200 vacation rentals in Beachmont.

  • Are there pet-friendly vacation rentals in Winthrop?

    Four-legged friends are welcome in Winthrop. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Winthrop?

    Yes! Work meets play with ease at over 90 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Winthrop vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Winthrop, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Winthrop?

    Winthrop has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in condo rentals in Winthrop?

    Experience the best of Winthrop with our condo rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Winthrop have air conditioning?

    Absolutely! We offer over 70 apartment rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winthrop have wifi?

    Absolutely! We offer over 80 apartment rentals with wifi in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winthrop have a gym?

    Absolutely! We offer over 10 apartment rentals with a gym in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Winthrop?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Winthrop

  • Total vacation rentals

    Explore 190 vacation rentals in Winthrop

  • Nightly prices starting at

    Winthrop vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 17,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    190 of Winthrop vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace 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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