Pet-friendly vacation rentals in Winthrop

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Top-rated pet-friendly home rentals in Winthrop

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

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Top guest favorite

A well-maintained backyard garden features a stone fire pit surrounded by seating. Flower beds with various plants provide color and texture. A wooden swing set and a shed are visible in the background, with a stone path leading through the grassy area.

Home in South Portland

4.91 out of 5 average rating, 116 reviews

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Guest favorite

A cozy living room is shown with hardwood floors and neutral-colored walls. A comfortable black chair sits beside a wooden coffee table adorned with a vase of flowers. Natural light fills the space through large windows, and a modern TV is positioned on a media console.

Apartment in East End

4.93 out of 5 average rating, 349 reviews

Haven on the Hill

Registration #2018-4091. On top of a quiet, leafy street in Portland's East End, our hippest neighborhood! Short walk to popular destinations like the Old Port, the ferry terminal, breweries and award-winning restaurants...plus water views, sea gulls, fog horns, running trails, sunrises and sunsets! NOTE: Please *do not book this space* if you can't honestly live by our House Rules. All guests must confirm that their group will abide by House Rules w/in 24 hours of booking to be confirmed.

Guest favorite

A serene waterfront scene captures calm waters dotted with boats gently bobbing in the harbor. Rocky shores lead to lush greenery in the background, with a clear blue sky above, creating an inviting coastal atmosphere in this Maine setting.

Apartment in Falmouth

4.96 out of 5 average rating, 153 reviews

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

Superhost

A welcoming outdoor patio area features two red chairs and a black grill, surrounded by neatly arranged gravel and stone pathways. Lush green grass and young plantings provide a natural setting. The entrance to the home is framed by a covered porch and decorative detail.

Home in Skowhegan

4.8 out of 5 average rating, 15 reviews

Cozy, Comfortable, welcoming With private suite

Keep it simple at this peaceful and centrally located place. This rental property is in walking distance of the historic area of downtown Skowhegan yet secluded enough to enjoy privacy while on your vacation. Local groceries stores, well-known eateries, and small business shops are just minutes away. Close location to lakes, fairgrounds (active depending on time of stay), movie theaters (Drive-in & Spotlight Cinemas), and more. You need quiet time, enjoy the private suite you’ll love it .

Guest favorite

A scenic view of the ocean is framed by a spacious lawn, with a wooden deck featuring a long bench. A well-groomed dog rests on a blanket beside the deck, with trees lining the property and a picnic table visible in the background.

Cottage in South Thomaston

4.95 out of 5 average rating, 104 reviews

Cottage by the sea private oceanfront shoreline

Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Top guest favorite

A mobile home is set within a spacious, grassy area, surrounded by trees and mountains in the background. A white picket fence delineates the property, while a small garden with flower beds is visible. The setting offers a peaceful, rural atmosphere.

Home in Andover

4.98 out of 5 average rating, 123 reviews

Cozy comfortable mobile home on private farm.

My place is close to the great outdoors! Hiking, biking, horseback riding, swimming and all water sports. We are an easy drive to three wonderful ski areas.. You’ll love my place because of the coziness, the location, the views and all the outdoor activities in the western mountains of Maine.. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). In season you can enjoy fresh vegetables from our gardens.

Guest favorite

A sandy beach area gently meets the water's edge, with calm waves lapping against the shore. A boat is visible in the distance, surrounded by lush greenery along the horizon, which creates a serene and natural setting.

Cabin in Bridgton

4.94 out of 5 average rating, 254 reviews

Cozy Cabin, Close to everything

Charming Cabin located on a dead end road in a wooded setting. Walk to Long Lake for a swim or 15 minute drive to ski slopes, 30 miles to North Conway, 60 minutes to Portland or just walk the town of Bridgton to visit the restaurants and antique shops. If you like to snowmobile the (ITS) trail is 200 feet outside the back door. The Perfect vacation spot. The house has Wi-Fi (GIG Access) which is plenty of bandwidth for work or play. Please read House Rules

Top guest favorite

A window view frames a serene landscape with snow-covered ground and distant mountains. Trees line the foreground, and a deck railing is visible, adding depth to the scene. Soft lighting enhances the tranquility of the natural setting outside.

Home in Greenwood

4.93 out of 5 average rating, 76 reviews

The Farmhouse at The Cross Farm

1910s farmhouse less than a mile from Mt. Abram main lodge, and 6 miles from Bethel and Sunday river. 3 private bedrooms sleep up to 6, with one full bath (with tub) on the first floor and a small half bath on the second floor. First floor laundry room. A back deck off of the kitchen has seating and a gas grill. Large full eat-in kitchen. Access to 80 acres (for walking and biking, but no motorized off-road vehicles are allowed), and approved pets are welcome!

Guest favorite

A private patio area is enclosed by a wooden fence, featuring a small dining table with two chairs. Potted flowers and ferns add color to the space, while string lights create a cozy ambiance. Natural light filters through leafy trees above.

Apartment in Portland

4.8 out of 5 average rating, 364 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

Guest favorite

A cozy fire pit area is surrounded by seven Adirondack chairs, offering comfortable seating for guests. Brightly colored cushions add a pop of color to the chairs. Large stones complement the gravel ground, while lush greenery frames the space.

Home in Conway

4.96 out of 5 average rating, 28 reviews

Wagging Tails Meet Hot Trails!

Welcome to our luxurious alpine escape, where every member of the family, including your furry friend, is invited to indulge in the ultimate ski getaway experience. Family-friendly luxury is our specialty, and that means your beloved dog is more than welcome to join in on the fun. Create unforgettable memories together in this idyllic retreat, where every moment is filled with warmth, laughter, and the undeniable magic of the mountains.

Top guest favorite

Home in Scarborough

5 out of 5 average rating, 6 reviews

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches

Experience the luxury of your own solar-powered, eco-friendly spa resort getaway in Maine! Enjoy a private spa in a four-season sunroom, featuring a heated indoor fitness pool (90°F) and a hot tub. Boost your immune system with hydrotherapy, then step outside to a sauna and fire pit—a truly indulgent retreat. Plus, we're just minutes from beaches, lighthouses, and Portland's Old Port!

Guest favorite

The exterior of a spacious townhouse is captured, showcasing a combination of large windows and a balcony. Comfortable outdoor seating is visible, complemented by landscaped elements such as flowers and rocks. The structure's architectural details reflect a classic design characteristic of the area.

Townhouse in Edgecomb

4.92 out of 5 average rating, 142 reviews

Joyful Maine Escape: 3 Bdr. Waterview Townhouse

A spacious townhouse to vacation with 3 bedrooms and view of the Sheepscot River. This stylish, relaxing townhouse is perfect for family and friends looking for a Maine retreat. Relax by the fire pit on the patio or on the balcony overlooking the Sheepscot River after a day of kayaking, antiquing, or an evening in nearby Wiscasset. Pets Welcome! Self Check In/Out