
Winthrop Holiday Rentals
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Our top choices for Winthrop holiday rentals

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
2. Steps from the ocean - minutes from Boston
Steps from the ocean - minutes from Boston
3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
4. Bright 2BR by Boston Waterfront
Bright 2BR by Boston Waterfront
5. Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown Boston
6. The Concord Hotel
The Concord Hotel
7. Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
8. Maverick Suites at 40 Temple St
Maverick Suites at 40 Temple St
9. Kasa Boston at Fenway
Kasa Boston at Fenway
10. Fun houseboat. Walk to Boston attractions WIFI
Fun houseboat. Walk to Boston attractions WIFI
11. Maverick Suites at 245 Newbury St
Maverick Suites at 245 Newbury St
12. Marriott Vacation Club® at Custom House, Boston
Marriott Vacation Club® at Custom House, Boston
13. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
14. The Chester Hotel
The Chester Hotel
15. Boston Financial District 1BR | Walk to anything!
Boston Financial District 1BR | Walk to anything!
16. Stunning Back Bay Studio Apartment
Stunning Back Bay Studio Apartment
17. Maverick Suites at 28 Fenway
Maverick Suites at 28 Fenway
18. Modern Studio | South End
Modern Studio | South End
19. Maverick Suites at 400 Columbus Ave
Maverick Suites at 400 Columbus Ave
20. Stellar South End Studio
Stellar South End StudioFind holiday rentals that suit your style
Top Winthrop Hotel Reviews

Arcadian Hotel
Find out more about Winthrop
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winthrop holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Winthrop. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winthrop. Seeing all the best attractions is bound to make you fall in love with Winthrop. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winthrop short-term rentals, that won’t be hard to do.




































































