Choose from 47 vacation rentals located in Winthrop, Massachusetts. Top filters in Winthrop include Internet / Wifi, TV, and Air conditioner. Prices range from $77 to $550 per night. Our most popular vacation rental types near Winthrop are Condo and Hotel.

Top vacation rentals in Winthrop

Front Entrance
5.0
Outstanding(111 Reviews)
Villa
 in Boston
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
10 guests · 4 bedrooms · 2 baths
Garden · Kitchen / 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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Beachfront
Property view
4.0
Good(223 Reviews)
Hotel
 in Winthrop
3star
Winthrop Arms Hotel Restaurant Logan Airport
Kitchen / 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 / Kitchenette, and more.

$$$$
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Terrace/patio
4.8
Outstanding(112 Reviews)
Cottage
 in Revere
Cape Cod style Oceanside cottage, near Boston, train, Airport
6 guests · 3 bedrooms · 2 baths
Garden · Kitchen / 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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Property view
4.2
Excellent(735 Reviews)
Hotel
 in Revere
Holiday Inn Express - Boston Logan Airport - Revere, an IHG Hotel
Pool · Pets allowed · Air conditioner

When traveling to Winthrop, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $94 per night.

$$$$
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Search by amenity

Vacation rentals with internet & wifi in Winthrop

Property view
4.0
Good(1 Review)
House
 in Revere
Pet-Friendly Revere Getaway, Steps from the T!
Pets allowed · Kitchen / 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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Pool
4.9
Outstanding(20 Reviews)
Condo
 in Winthrop
Cody's Place Winthrop Boston Logan Airport Beaches
2 guests · 1 bedroom · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Winthrop? This Condo offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$
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Revere Vacation Rental | 2BR | 1.5BA | 2 Stories | 1,100 Sq Ft | Stairs Required
5.0
Outstanding(28 Reviews)
House
 in Revere
Pet-Friendly Revere Getaway, Steps from the T!
4 guests · 2 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Air conditioner

This House for $324 in Winthrop, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
5.0
Outstanding(29 Reviews)
Condo
 in Winthrop
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
6 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Winthrop? Our Condo 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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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 $77-$550. The average price for rentals in Winthrop is $179 per night.

What are the most popular vacation rental amenities in Winthrop?

  • Internet / Wifi
  • TV
  • Air conditioner

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