Holiday rentals in Winthrop

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Top-rated holiday rentals in Winthrop

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

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Top guest favourite
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, 1,349 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.

Guest favourite
The spacious guest suite features a comfortable queen-sized bed with a wooden frame, a kitchenette with modern appliances, and a small dining table with two chairs. Light-colored vinyl flooring extends throughout the room, enhancing the airy ambiance.
Guest suite in Revere
4.92 out of 5 average rating, 361 reviews

Private Studio 10 min from Airport

Private guest suite is centrally-located for easy access to the city. Professionally cleaned. You’ll have a private entrance to come and go as you’d like with a code keypad door. Our newly renovated BASEMENT 500 sq ft is perfect for a guests to escape for a few days. Private bathroom and kitchenette, 10 min away from airport. Bus and train station walking distance. 15 min walk to Revere Beach We are in close proximity to Downtown Boston as well as Salem and other areas. Free wifi Street parking

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, 264 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 favourite
Apartment in Winthrop
4.99 out of 5 average rating, 209 reviews

Truly Ocean-Front! Spacious Family Home w/ Pets

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 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, 148 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
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
4.96 out of 5 average rating, 164 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 exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.
Cottage in Winthrop
4.98 out of 5 average rating, 483 reviews

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

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
4.88 out of 5 average rating, 225 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.

Superhost
The exterior of a two-story blue house is presented, featuring a brick facade and multiple windows. A covered porch with stairs leads to the entrance, surrounded by neatly trimmed shrubs. Sunlight illuminates the scene, highlighting the clear blue sky.
Flat in Winthrop
4.75 out of 5 average rating, 194 reviews

The Price is Right Boston Airport Beach Park Free

Private spacious 1 bedroom 1 bath attic apartment with new rug/paint/ac. Nice little skyline view of Boston in a beautiful safe quiet residential neighborhood. Great place to rest your head or use as a base to Boston The Encore Casino Salem & beyond! Bedroom comfy mattress/sheets 55” Smart TV blackout shade ceiling fan nightstands lamps 2 chairs Living Areas sofa bed 55” Smart TV sitting chair table 2 chairs/lamps Kitchenette fridge microwave Keurig toaster oven dishes silverware glass

Superhost
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.

Guest favourite
A spacious studio apartment is presented, featuring a full bed with soft linens and decorative pillows. Natural light fills the room through large windows, which are dressed with elegant curtains. A modern seating area includes a sleek black sofa and an armchair, creating a comfortable relaxation space.
Flat in Beachmont
4.84 out of 5 average rating, 197 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 favourite
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, 985 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.

Popular amenities for Winthrop holiday rentals

When is the best time to visit Winthrop?

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Avg. price$158 SGD$164 SGD$194 SGD$195 SGD$216 SGD$216 SGD$221 SGD$231 SGD$206 SGD$221 SGD$193 SGD$177 SGD
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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 2,550 vacation rentals in Orient Heights, over 200 vacation rentals in Point Shirley, 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!

  • Do house rentals in Winthrop have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Winthrop. Enjoy a tailored experience with all the comforts you desire.

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

    Experience the best of Winthrop with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Winthrop have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning 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.

  • Are there family-friendly condo rentals in Winthrop?

    Winthrop has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 80 homes with wifi, over 70 homes with air conditioning, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Winthrop

  • Total holiday rentals

    Explore 190 holiday rentals in Winthrop

  • Nightly prices starting at

    Winthrop holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    180 of Winthrop holiday rentals include wifi 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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