Winter Hill pet-friendly rentals

We found 72 pet-friendly rentals — enter your dates for availability

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September 2025

October 2025

Explore Winter Hill pet-friendly rentals

Quiet Low-Key Boston Get Away

Sleeps 10 · 2 bedrooms · 1 bathroom

Premier Host

4BDR/2.5BA APT Near Tufts/7 min-Walk to Subway/Free Parking for 2 cars

Sleeps 9 · 4 bedrooms · 2+ bathrooms

Top rated pet-friendly rentals - Winter Hill

Premier Host

Great

So easy to access and clean, everything we needed

Joni P.

Stayed Apr 2023

Premier Host

Convenient, spacious and well equipped and

Union Square is a great little location with everything you need including a T stop. The free street parking was excellent and everything worked smoothly. The stairs to the top level rooms are steep but with hanging hammock chairs, a climbing wall and space to spare it was all worth it.

Stephen K.

Stayed Dec 2022

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