
Pet-friendly vacation rentals in Winthrop
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Top-rated pet-friendly home rentals in Winthrop
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Pet-friendly house rentals

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN
Thanks Jo for the accommodation. This place was meeting our requirements, our stay was pretty comfortable. It was warm, clean and my 3 yr old enjoyed the backyard. Jo was approachable and friendly to talk. I would definitely recommend this place.

Welcoming 7-room house <15 miles to Boston & Salem
Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃

Entire House Near South Shore Hospital/Whole Foods
My groups stayed at Trang’s home for 2 night and our stay was perfect. The home was exactly as pictured in the listing and was very clean and spacious. Check-in instructions were straight forward and easy to understand. Would definitely stay again in the future if we ever find ourselves in the area.

Absolutely Gorgeous 3 Bedroom Close to Boston
This is the second of Domenic's properties I have stayed at and they never fail to be extremely clean and welcoming. The beds are comfortable and Domenic is a responsive host. Looking forward to our next visit!

Newly renovated, spacious, clean, 3 bedroom home.
Our family had a wonderful stay at the house. Extremely clean, comfortable, with so many amenities and thoughtful touches to make you feel right at home. We really enjoyed the deck with comfortable seating and sun umbrella. Most highly recommend!

Comfortable house w garden and parking, close to T
Great stay: - Easy check-in/access — we arrived very late at night and entry was well lit and straightforward - House was cozy with effective and responsive heating (we stayed during cold weather, so this was a big deal) - Clean house, comfy beds, variety of pillows (soft to v hard) - Easy check-out with zero weird instructions/requests - Host super communicative for basic Q&A I’d book again! Thanks!

Cozy house close to Boston
Karen’s home truly is cozy. We were here two weeks before Christmas and it was decorated and beautiful. Beds are comfortable, the kitchen was clean and well stocked, nice big fluffy towels and I loved the shower! We have stayed in several,places in the Boston area and this is one of the best. Even my dogs loved it!

Lovely 2 Bedroom Victorian 1.5 Blocks To Ocean!!!
This Airbnb was one of the best we ever had stayed in! Her house was beautiful, cozy and clean! Johanna was a great host and would definitely love to stay here again!!
Pet-friendly home rentals with a pool

Large Pool, Nature Trails, Redd's Pond, 4-Bed
Everything was as listed and very responsive and great host. The property was in a very nice and in a great town. We enjoyed our time there.

Beautiful Spacious 4BRM House!
Maxine anticipated every possible need and so much more available. She went beyond any host I have ever stayed with and I travel quite often. I highly recommend Maxine's place

the house of id; vintage shop, accessible space
This has to be the neatest little place on Airbnb in the Boston area, and that's something to be said. Paige and Dara described the place and the experience perfectly, were a dream to communicate with, and were overall humorous hosts. Their in-house shop was very entertaining for us. We will absolutely be staying here again in the future.

Cozy Private Suite halfway between Cape & Boston
Great place to stay in a super convenient location for driving places. There was event a snowstorm during our stay and the hosts made sure to have the walkway and driveway clear for us to get in and out with ease!

Modern Space With Pool Close To Singing Beach
This property was precisely as advertised, ideally located for my needs, and Ian was a very responsive host. I would recommend the property and the host without reservation.

In-town 2 bedroom beach cottage with a pool
This house is a true gem. The home is cozy and welcoming with lots of puzzles and family games to play. The pool is pristine and was so much fun to use. The beautiful trees and flowers provide nice shade and privacy around the pool while also feeling like you’re inside a pollinator garden. The home is an easy walk to front beach and bearskin neck where we enjoyed good restaurants and shops. Trenton and Cassie are great hosts- very responsive and friendly. We hope to stay here again!

Spacious 3-BR Furnished Beach Home
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!

Lovely 2- bedroom serviced apartment with pool
This apartment was well appointed, clean and very well located. The host was friendly and responsive. We enjoyed our comfortable stay and would recommend!
Private, pet-friendly home rentals

A Cozy 3 Bedroom Home Close To Boston & Parking
Wonderful stay! Shirley was a responsive and kind host and we enjoyed staying here for three nights over the Boston Marathon weekend. Squeaky floors may make it tough to make a midnight trip to the kitchen or bathroom unnoticed, but everything else was perfect. Would stay here again.

Hillside Ocean View 2BR with Private Beach Access
We love Ipswich and are so glad to find this gem of Airbnb. Mark's communications are topnotched and he proactively checked in with us to ensure that everything is alright. The house has everything we needed and more....not just for short stays but equally suitable for longer stays too. The bed and pillows were very comfortable. The house heating system is very efficient and heats up the whole house quickly and comfortably for the few cold days we were staying there. My husband loved having a dedicated work space which had a beautiful water view. There were plenty of supplies in the kitchen, bathroom and laundry. Everything is very well thought out. It might be an older house but it's very quaint, cosy and quintessentially New England. Although we had several days of lousy weather.... we still managed to do plenty out of the few half days when the skies cleared out. Oh and thank you for the very lovely cranberry banana bread... its one of the best that we've ever eaten.

Charming Studio downtown Salem, MA *Parking
Daliana’s apartment was perfect for our weekend away in Salem with our pup! We didn’t need to use our car for our entire stay as everything we wanted to see or do was just a short walk away. The apartment was clean and cozy. Thank you for hosting us!

"COZY NEW 1BR GUEST SUITE SLEEPS FOUR "
Lino and Wendy were great hosts! The location is absolutely stunning with great views in the surrounding areas. It’s very close to Salem and Boston, which makes it a great and super convenient place to stay! Thanks again lino and wendy

Historic JP Brownstone with Parking. Pets Welcome!
The historic brown stone was very nice, immaculate and spacious. There is a parking spot close to entrance. There is a modern bathroom on same floor as bedroom. The bedroom is on one floor and spacious kitchen on upper floor. With the t directly behind the building you can hear the train except for a brief period of time in the middle of the night. Despite the noise we would stay here again. A lovely place .

West Cambridge 2BR: Pet OK, A/C, backyard, lovely!
Accommodations were exactly as described. Lower level of a duplex with a young family upstairs. Host was very responsive and helpful. Kitchen was well equipped. Back deck was really peaceful and quiet.

Boston/Quincy- Walk to Red Line Train-Free Parking
We had a lovely time staying at Julie's unit. My husband and I and our small dog enjoyed our stay. Julie is very easy to communicate with and responsive. The bed is comfortable in a spacious bedroom. The other areas are comfortable and nice. I used the office area to work and appreciated the additional monitor and spacious desk. The unit is conveniently located near two large grocery stores, Star Market and Shop N Stop, and numerous restaurants a few minutes to get to. We ate outdoors with our dog at the seafood restaurants by the beach and also enjoyed a lot of take out from the numerous Asian restaurants on Hancock. It was handy to be able to use the washer and dryer downstairs. We appreciated the on premise parking space. The neighborhood felt quiet and safe. We took frequent walks with our small dog and the neighbors are friendly. There are many appliances to use including two coffee pots, spices, and condiments. Julie is a great host. We would stay again.

Walk to Good Harbor Beach
Felt welcome and comfortable from the start. It exceeded my expectations and met all my needs. I felt comfortable bringing my dog who was also welcomed. Great experience and responsive host. Thanks
Quick stats about vacation rentals that are pet-friendly in Winthrop
Total rentals
50 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Brown University
- New England Aquarium
- Sandwich Glass Museum
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Onset Beach
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Boston Public Library
- Crane Beach
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- Pinehills Golf Club
- Aaronap Cellars
- John Hancock Tower
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