Pet-friendly vacation rentals in Winthrop

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winthrop

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favourite
A modern living area features a spacious sectional sofa with decorative pillows, facing an open kitchen fitted with sleek cabinetry and bar seating. Large windows provide natural light, while plants are displayed on shelves, enhancing the contemporary design.
Apartment in East Boston
4.95 out of 5 average rating, 151 reviews

Luxury Penthouse w/ Private Roof Deck By The Ocean

Take in the beautiful skyline view as you have your morning beverage of choice, then take a relaxing stroll along the harbor walk 1 minute to the harbor 5 minute uber / 10 minute walk to airport 15 minutes to downtown Boston (by MBTA or uber) ON STREET PARKING: Only free 6P-8A and on the weekend. There is a $2.50 toll to drive into the city. Spot hero is a parking app that works great in Boston also. PARTIES: Not allowed. This is a family neighborhood. No loud music. Quiet hours after 9pm.

Top guest favourite
A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.
Guest suite in Winthrop
4.92 out of 5 average rating, 1,349 reviews

Licensed Boston airport studio 5 stars, subway

We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

Guest favourite
A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.
Cabin in Cohasset
4.92 out of 5 average rating, 353 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

Top guest favourite
A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.
Apartment in Nahant
4.94 out of 5 average rating, 156 reviews

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

Top guest favourite
Condo in Winthrop
4.99 out of 5 average rating, 209 reviews

Truly Ocean-Front! Spacious Family Home w/ Pets

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Guest favourite
A spacious bedroom features a large bed dressed in white sheets and a light blue blanket. Nightstands with lamps are positioned on either side of the bed. A subtle area rug adds warmth, while a painting hangs on the wall, complementing the calm color scheme.
Apartment in Beachmont
4.96 out of 5 average rating, 148 reviews

Spacious 3 Bedroom Apartment with King Bed

Family friendly, walk-out basement style apartment close to everything! Clean and safe neighborhood. A 10 minute walk to two beaches: Revere Beach - America's first public beach & Short Beach - a neighborhood favorite. 5 minute walk to Beachmont T station and bus lines - 15 minutes to Downtown Boston! 10 minute drive to Logan or 20 minute drive to the Casino. 25 minute drive to Salem. Walkable to an Italian Bakery, Dunkin Donuts and Starbucks as well as a number of restaurants and eateries.

Guest favourite
Apartment in Coolidge Corner
4.98 out of 5 average rating, 151 reviews

New Luxury 2B2B Apartment, One Free Parking

This is a NEWLY renovated, luxurious 2B2B apartment. Comes with high-quality linens, towels, cookware and tableware. Location is Great, A short walk to T-Stop, restaurants, cafés, groceries and more. 1 mile to Longwood Medical Area , Fenway and BU. Pets friendly, need to be approved prior to booking. additional $200 per pet will apply. Our places are professionally cleaned & sanitized. bleached Linens and towels. Separate Air conditioning and heating system to avoid the crowds at hotel.

Superhost
An aerial view captures a landscaped pool area featuring a long, rectangular plunge pool surrounded by a spacious deck. Multiple lounge chairs are arranged neatly along the water's edge, while shaded seating areas are provided by large umbrellas, promoting relaxation in a vibrant outdoor setting.
Apartment in Charlestown
4.89 out of 5 average rating, 103 reviews

Lux 2BR Apt w/ Pool and Gym

Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

Guest favourite
A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.
Home in East Boston
4.77 out of 5 average rating, 220 reviews

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Guest favourite
A micro studio space features a wall-mounted television positioned near a built-in bookcase. Natural light enters through two large windows, illuminating the minimalist decor and a cozy, spacious bed with crisp white bedding. A small white table and chair enhance the functionality of the room.
Apartment in Fort Hill
4.9 out of 5 average rating, 918 reviews

AKBrownstone: cozy private studio by T

🏠 Live like a local: designed micro studio, in a classic Boston Brownstone 🌳 Your very own cozy 170sqft (15sqm) pied-à-terre on the ground level, overlooking Victorian homes on a tree lined street 🚇 5 mins walk to the T (subway), 3rd stop to Back Bay city center or go on bike & walking path 👣 Walk to Longwood Medical Area (Harvard Medical, etc), Museums (MFA, Gardner), Northeastern, & Fenway Park 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Superhost
A light-filled living area features a white sofa adorned with plush cushions, accompanied by two rattan chairs. A round coffee table is positioned centrally on a soft rug, with a small potted plant placed atop it. Natural light streams in through a nearby window.
Apartment in Roxbury
4.96 out of 5 average rating, 107 reviews

Newly Renovated + Spacious Apt w/ Parking

Our newly renovated space in Roxbury offers comfort and style. Creature comforts and amenities are plentiful in this spacious, bright apartment. You'll love sleeping on the luxury organic latex mattresses and enjoy the spacious interiors and modern, well-appointed kitchen. Cozy up in front of the big screens and stream your favorite movie or the next big game. Conveniently located to public transportation and easy access to all Boston offers - the ideal getaway!

Guest favourite
The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.
Condo in East Boston
4.93 out of 5 average rating, 219 reviews

Family Home + Near Downtown + Cool Backyard!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

Popular amenities for Winthrop pet-friendly home rentals

When is the best time to visit Winthrop?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$170 CAD$168 CAD$189 CAD$210 CAD$241 CAD$250 CAD$250 CAD$293 CAD$248 CAD$257 CAD$194 CAD$182 CAD
Avg. temp-1 °C0 °C4 °C9 °C15 °C20 °C23 °C23 °C19 °C13 °C7 °C2 °C

Quick stats about vacation rentals that are pet-friendly in Winthrop

  • Total vacation rentals

    Explore 50 vacation rentals in Winthrop

  • Nightly prices starting at

    Winthrop vacation rentals start at $98 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Winthrop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winthrop rentals

  • 4.8 Average rating

    Winthrop stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Winthrop’s top spots, include Orient Heights Station, Beachmont Station, and Suffolk Downs Station