
Pet-friendly holiday rentals in Winthrop
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Winthrop
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Popular amenities for Winthrop pet-friendly home rentals
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.

Great for Families Modern Farmhouse Near Shopping
Gil’s home was just like the pictures! Great home in a perfect location in Salem Nh. Gil was also super responsive all throughout from when you book until you check out! Definitely recommend this home!

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.

Rockport Pool House|4BR/3BA Walk to Bearskin Neck
Great space. Loved that it was dog friendly. My older lab appreciated the amount of space! Kids enjoyed themselves and the neighborhood was quiet and the few people we ran into were very friendly.

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
We stayed at this property for 3 nights and felt right at home. It was very clean and comfortable. The owners are very friendly and respond very quickly. The instructions they left couldn’t be more clear. We definitely recommend and cannot wait to stay here another time in the future!

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!
Private, pet-friendly home rentals

Salem's Enchanted Inn
Such a perfect place. Super soft towels, comfy bed, perfect little kitchen w everything we needed. Gave us great ideas for things to do during our stay and even tips to avoid the traffic coming into town. Would recommend!!

Hillside Ocean View 2BR with Private Beach Access
Mark’s place was retro and quaint. It brought back special childhood memories of the house I was raised in back East. We loved our time here. This home is cozy and welcoming and has everything you could need to enjoy your stay. Mark provided homemade banana bread and coffee. That was very much appreciated since we didn’t arrive until 11 pm and there were no stores open. The views were very cool and a great place for birdwatching. It’s a short walk to two different beaches and a friendly neighborhood to walk through. Ipswich is a wonderful town with lots of things to see and do. We would definitely like to book this place again. Thanks Mark.

"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!
Was an amazing Place to stay. The area was outstanding with lots to do and very easy access to the train to get to and from downtown and other areas of the city. Will definitely stay here again! The parking spot was a huge plus!!

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.

Harbor Hideaway
What a find! I came to Kristen's because some plans fell through last minute. Having never heard of Marblehead but keen to visit somewhere by the sea and easily accessible from Boston, wow did I get a pleasant surprise. It is absolutely beautiful there, I had to pinch myself - it was like living in a film! The apartment was absolutely perfect. I'd been staying somewhere a bit grubby and disorganised beforehand and Kristen's place was absolutely sparkling clean, I felt incredibly welcome and cared for right away. Furthermore, checking in early with my monstrous suitcase was no problem at all and the apartment is generously stocked with coffee, tea, snacks, a bottle of wine, cold drinks, a folder of local recommendations, comfortable, quality furnishings and linens, great lighting and more. This is what true hosting is all about if you ask me - making your guests feel as comfortable and welcome as possible and Kristen most certainly does this in spades.

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 holiday rentals that are pet-friendly in Winthrop
Total rentals
50 properties
Nightly prices starting at
£52 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
Destinations to explore
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- Hampton Beach
- Boston Common
- Revere Beach
- Salisbury Beach
- TD Garden
- Fenway Park
- Wingaersheek Beach
- Jenness Beach
- Humarock Beach
- Lynn Beach
- Duxbury Beach
- Harvard University
- Saquish Beach
- Wallis Sands Beach
- Coffins Beach
- North Hampton Beach
- Brown University
- Monument Beach
- Little Harbor Beach
- Herring Cove Beach
- New England Aquarium
- Sandwich Glass Museum
- Faneuil Hall Marketplace
- Sagamore Beach