178+ Rental Villas and Private Getaways in Winthrop |
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Winthrop Vacation Rentals & One Degree Stays Homes

About Winthrop Vacation Rentals

There are more than 178 vacation rentals that are available in Winthrop. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Winthrop.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Winthrop, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Winthrop. Places to stay near Winthrop are 739.25 ft² on average, with prices averaging US $294 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Winthrop with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Winthrop

Type Count
Holiday Apartments 109
Vacation Homes 23
Villas 2

Use these Quick Filters to Find a Vacation Rental in Winthrop

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winthrop.

Weather in Winthrop, MA

View the weather forecast for Winthrop before booking your Winthrop Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winthrop, MA

OneDegreeStays offers a large selection of top attractions around Winthrop. Research things to do on your vacation before you visit Winthrop.


Winthrop Beach
Donovan Beach
Point Shirley Beach
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
Massachusetts Institute of Technology

Other Places to Stay in Winthrop, MA


Donovan Beach 335 Properties
Winthrop Beach 132 Properties
Point Shirley Beach 85 Properties

Frequently Asked Questions About Winthrop?

What are the top vacation rentals in Winthrop?

There are a lot of options in Winthrop. If you plan on staying in the Winthrop area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winthrop:

How many vacation rentals have private pools in Winthrop?

There are 1 vacation rentals with private pools near Winthrop. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Winthrop are best for families?

If you are looking for a family-friendly vacation home in Winthrop, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winthrop:

How many onedegreestays vacation rentals are available in Winthrop?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 178 in the Winthrop area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Winthrop. 

Nearby Neighborhood (2) 
Neighborhood Property Count
East Boston Vacation Rentals in Boston, Massachusetts 70
Harbor View - Orient Heights Vacation Rentals in Boston, Massachusetts 302

People Also Ask

There are 178 Winthrop, MA Vacation Rentals

Recently Booked Vacation Rentals in Winthrop