Choose from 66 vacation rentals located in Winthrop, Massachusetts. Top filters in Winthrop include Internet / Wifi, Air conditioner, and Parking. Prices range from $92 to $2,605 per night. Our most popular vacation rental types near Winthrop are Apartment and Hotel.

Top vacation rentals in Winthrop

Interior
5.0
Outstanding(120 Reviews)
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
Villa
 in Boston
10 guests · 4 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Winthrop? Our Villa might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Property building
3.9
Good(9,447 Reviews)
Hampton Inn Boston Logan Airport
Hotel
 in Boston
3star
1 king bed
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Winthrop at Hampton Inn Boston Logan Airport for $128 for your next trip.

$$$$
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Beachfront
Property building
4.0
Good(259 Reviews)
Winthrop Arms Hotel Restaurant Logan Airport
Hotel
 in Winthrop
3star
1 queen bed
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Winthrop with a stay at Winthrop Arms Hotel Restaurant Logan Airport, a top rated Hotel with amenities such as Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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Terrace/patio
4.9
Outstanding(137 Reviews)
Cape Cod style Oceanside cottage, near Boston, train, Airport
Cottage
 in Revere
6 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Cottage in Winthrop has everything you need for a rejuvenating stay. Treat yourself to Cape Cod style Oceanside cottage, near Boston, train, Airport's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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Vacation rentals with internet & wifi in Winthrop

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Outdoor dining
5.0
Outstanding(105 Reviews)
Ikram's Place so close to Boston, Subway & Logan international Airport
Apartment
 in Revere
5 guests · 2 bedrooms · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner

This Apartment in Winthrop, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property view
4.0
Good(1 Review)
Pet-Friendly Revere Getaway, Steps from the T!
House
 in Revere
Pets allowed · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Winthrop? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Fridge, microwave, oven, stovetop
4.8
Outstanding(71 Reviews)
Luxury, New 2-Bedroom Condo Near Airport/Boston/Train
Apartment
 in Boston
5 guests · 2 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Winthrop in our Apartment, Luxury, New 2-Bedroom Condo Near Airport/Boston/Train. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
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Property view
4.0
Good(1 Review)
Waterfront Retreat with Deck about 7 Mi to Boston!
House
 in Winthrop
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Winthrop? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Winthrop

Winthrop travel guide

Let us help you plan your perfect Winthrop vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winthrop, and more.

Frequently asked questions

What do I need to know before visiting Winthrop, MA?

Before visiting Winthrop, MA, it is important to know a few things.

  • The town has a population of over 18,000 people.
  • It is located on a peninsula in the Boston Harbor.
  • The town is home to many parks, beaches, and other recreational areas.

Whether you are visiting for the day or planning a longer stay, Winthrop offers plenty to do. There are plenty of restaurants, shops, and attractions to explore. Additionally, the town is known for its rich history and vibrant community.

What are the must-visit tourist attractions in Winthrop, MA?

Winthrop, MA is a beautiful seaside town with plenty of must-visit tourist attractions. Here are some of the top spots to check out:

  • Winthrop Beach
  • Deane Winthrop House
  • Winthrop Center Historic District
  • Winthrop Yacht Club

These attractions offer a great opportunity to explore the town's rich history, take in the stunning views of the ocean, and enjoy the many activities that Winthrop has to offer.

How can I get around in Winthrop, MA?

You can get around in Winthrop, MA using the following methods:

  • Public transportation - MBTA buses, the Blue Line, and the Commuter Rail
  • Walking or biking on the town's many paths and trails
  • Rent a car from one of the local rental companies

Where can I find affordable accommodation in Winthrop, MA?

Winthrop offers a variety of affordable accommodations to suit any budget. Here are some of the top options:

  • The Winthrop Beach Hotel & Suites offers excellent value for a family-friendly stay.
  • The Winthrop Inn provides comfortable rooms at an affordable rate.
  • The Winthrop Harborview Inn is a great option for budget-conscious travelers.
  • The Winthrop Yacht Club offers luxurious suites at an affordable price.

No matter what your budget is, Winthrop has something for everyone. With a wide range of accommodations, you’re sure to find the perfect place to stay.

What is the culture like in Winthrop, MA?

Winthrop, MA is an oceanfront community located just outside of Boston. It is a vibrant, diverse, and close-knit community that is home to a wide variety of people and cultures. Here are five points that capture the essence of the culture in Winthrop:

  • A strong sense of community and camaraderie
  • A deep appreciation for the town's history and natural beauty
  • A commitment to the environment, with a focus on sustainability
  • An emphasis on education and the arts
  • A commitment to helping those in need

Is Winthrop, MA safe to travel to?

Winthrop, MA is a safe place to travel to. Here are some reasons why:

  • Low crime rate
  • Friendly locals
  • Plenty of activities to do

Whether you're visiting for a weekend or staying for a week, you can rest assured that Winthrop, MA is a safe place to travel to.

What are the popular shopping destinations in Winthrop, MA?

Winthrop, MA is home to some of the best shopping destinations in the area. Here are some of the popular spots:

  • Winthrop Center Mall
  • Winthrop Marketplace
  • Winthrop Square Mall

These shopping destinations offer a variety of retail stores, restaurants, and entertainment options for residents and visitors alike.

What are the best neighborhoods to visit in Winthrop, MA?

The best neighborhoods to visit in Winthrop, MA are:

  • Point Shirley
  • Crest Avenue
  • Suffolk Downs

These neighborhoods offer a variety of attractions, such as beaches, parks, restaurants, and shopping centers.

Where is Winthrop, MA?

Winthrop, MA is a town in Suffolk County, about 5 miles northeast of downtown Boston. It is situated directly on Boston Harbor and features a town beach, a harbor walk, and a number of parks and recreational areas. It is known for its small-town atmosphere and close proximity to the city of Boston.

What are the most popular vacation rental amenities in Winthrop, MA?

The most popular vacation rental amenities in Winthrop, MA include:

  • Fully-equipped kitchens
  • Outdoor spaces like decks, patios, and balconies
  • Modern appliances and fixtures
  • High-speed internet access
  • Beach access

These amenities provide visitors with all the comforts of home while also giving them access to the area’s beautiful beaches and attractions. Many rental properties also feature luxurious amenities like swimming pools, hot tubs, and saunas.

What are the top things to do in Winthrop, MA?

Winthrop, MA is a great place to visit for a variety of activities. Here are the top things to do in Winthrop, MA:

  • Visit the Winthrop Beach
  • Explore the Deer Island Park
  • Take a ride on the Winthrop Ferry
  • Shop at the Winthrop Marketplace

Whether you’re looking for a day of relaxation or adventure, Winthrop, MA has something for everyone. From the beach to the ferry, you can create an unforgettable experience.

What is the price range for rentals in Winthrop?

Vacation rentals in Winthrop have a price range between $92-$2,605. The average price for rentals in Winthrop is $156 per night.

What are the most popular vacation rental amenities in Winthrop?

  • Internet / Wifi
  • Air conditioner
  • Parking

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