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

Sunny 2-BR 5 min to Bates & River Trails
This is the 2nd time I've stayed at Emma's place. I came both times for a workshop and ceremony that took place in both Freeport and in Portland. Drives to Portland were the longest, and not too taking, and I chose to stay at Emma's place BECAUSE of the way the house holds me: the spaciousness, the attention to art and wisdom, the lighting and unfussy-yet-design-inspired furniture choices, the plant life, the textures and colors: all these things are soothing and welcoming. It was a pleasure to drive "home" exhausted, knowing what it feels like to open that back door.

Oak Leaf
Enjoyed our stay very much! Lovely location on the water. Some white traffic noise but worth it watching the boats and wildlife! Comfy bed. We slept very well. Well-stocked kitchen. The location is perfect for lots of little day trips. Our only disappointment was the size of the smallest room. It’s very tiny. Great for a child but pretty tight for our adult son. Host was attentive. We will be back!

Cheerful spacious updated 1825 Maine Farmhouse!
We had family in town for graduation and Amy’s place checked all the boxes for us. Plenty of room to spread out yet still be together. The bedrooms were roomy and cozy. Our little nephew loved the well-stocked bookcase that allowed him to have a different story every night. The trampoline and outside space were wonderful. We even used the barbecue. Would definitely recommend!

LUX Designer Private Waterfront
We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!
This house was perfect for me and my guests! All 7 of us fit perfectly, It didn’t feel too overcrowded! We loved the beautiful view off the deck and the hot tub was an amazing touch! The house was very clean and had everything we could’ve needed. I loved how clear the instructions were for everything and how responsive the hosts are if you need anything!

Summer River Retreat with Hiking Trails
By far one of the best Airbnb’s we’ve ever stayed at. Superb location, beautiful river view in front and forest view (with trails) in back. Plenty of garden space to run around in with the kid(s). And only a 5-minute drive into quaint and charming Bath. The place itself was beautifully laid out, with so much space and comfort. Pip was always available, efficient and kind and to communicate with. Cannot recommend this place enough if you’re looking respite in nature, comfort in home, and proximity to town.

Rustic Farmhouse at Oxbow Brewery
My husband and in-laws and I and our two dogs stayed for a long MDW. The weather did not cooperate but did not hinder us. Especially staying at this Airbnb on the beautiful Oxbow Brewing property. In fact the coziness of the space made a rainy day even more fun. We were visiting for the racetrack and location was excellent for privacy and also close to local attractions. Wish we had more of a group to experience the space with us, it was really special!

The Winter House
Beautiful setting on the lake with a modern, updated home complete with so many thoughtful amenities and touches - would love to return!! Spectacular sunsets and a private dock, too - did some late summer fishing on the Kennebago and the Magalloway - spectacular!
Pet-friendly home rentals with a pool

Large Home with Great View next to horse farm
Beautiful and peaceful place! Just admiring the surroundings let the peace and tranquility set in and consume you. Highly recommend! Teresa is a wonderful host and flexible to your needs. Will definitely visit again, thank you Teresa!

A+ Views -Jet Spa Tub Sauna Sunset/Stars
Jonathan and Lisa were wonderful hosts! We stayed 3 nights to enjoy some Spring skiing at Saddleback. The home was close to town and a quick drive to Saddleback mountain. The house is perched high on a hill overlooking Rangeley lake. The downside is that the driveway is steep and icy (this time of year due to the recent March thaws) but the view and sunsets are breathtaking!! For an additional fee, you can enjoy their newly built sauna and whirlpool. So relaxing after a day of skiing that we booked it twice. The house has all the comforts of home. Being culinary masters, we had a bit of a struggle in the small kitchen. But certainly most everything you need to prepare great meals. Communication with the hosts was excellent and timely.

The 1785 Suite, Amazing Views, Walk to River
loved this layout! this place had it all!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

A place to be The Hidden Gem Mt Vernon, Me
The host gave us an upgrade to another tiny house in the same location that we gladly accepted. We were welcomed by fresh lilacs in the tiny home with cozy ambiance. The location is remote with a small farm stand (the honey from this stand is a must, we got the biggest jar and we have zero regrets). This is a peaceful retreat with beautiful views and hikes. I recommend this to anyone looking to escape the city.

Steep Falls Escape, river & falls just steps away
We loved our stay! A week was not long enough! Very open layout with lots of space. We loved having a washer and dryer! It was a pleasure to talk to Tom! Really a person you could talk to hours for! We left feeling like family, and couldn’t recommend the place more! If you’re looking to visit Maine or even the big city of Portland, I would recommend you look here. Being out in the country sheds a different light on all that Maine has to offer!

Cozy Apartment with In-Town Convenience
I had a great month exploring Maine with my dog from this garage apartment. The owners are friendly but not intrusive. Some days my dog and I just laid a blanket on the grass and sat in the beautiful backyard. Go to Pickles Potions and get the body oil, it helped me keep bugs away.

Cabin on the hill!
I was meeting with family for a graduation. Four of us were staying here. The place was exactly what we needed in our lives and hoped for. It was country, quiet, peaceful and beautiful. It was so beautiful sitting on the back porch that we never once sat in the living room. We had lots of coffee and laughs sitting out there. We never even went into the hot tub or sauna. Would definitely recommend if this is what you need for your soul.
Private, pet-friendly home rentals

Golden Pine Farm
absolutely beautiful property in the heart of Maine, reccommend this place to any party looking for accommodations in and around the area! 5 stars

Bluebird Cottage on Woodbury Pond
Justin’s house was spacious and clean and had everything we could need. The kitchen is fully equipped and when we were there it all seemed brand new. Beds are comfortable and the upstairs loft bedroom is a great space. Every amenity was provided! We were not able to take advantage of the lake due to the weather. We didn’t realize when we booked that the house is right off the road and is part of a cottage community development that is still being built. Nevertheless, it was peaceful and quiet and lovely to be steps from the lake and to be near so many places in central Maine. We highly recommend a stay here.

Lakeside Cottage Tacoma Lake
So good I almost don’t want to leave a review because it feels like giving away a secret! We explored the nearby nature trail, went canoeing everyday, and our 3 year old loved playing at the little beach right off the property doorstep. Eric was responsive, proactive, and went out of his way to make sure our stay was memorable for us and our little one. Highly recommend!

Lakefront Dome Home w/deck and dock
Great dome house! Beautiful location on the lake! Plenty of room for the five of us! The kids loved the loft! Beds were so comfortable! Kitchen had everything for cooking! No need to leave if you rent in the summer. Hannaford 10 minutes away!

Year Round Cabin in Litchfield
great place to stay. We hosted Christmas dinner with our smallish family and it easily accommodated everyone. Highly recommend staying here

Modern lakefront log cabin with sunset views.
Beautiful place. Perfect getaway. Paul was very nice and helpful. Great recommendations for places to go. Very responsive to any questions we had. I could sit on the deck for days and watch the pond and soak up the sun. Only regrets was we had more rain than sun and unable to enjoy a bonfire. But thats Maine. Lol Cant wait to plan a trip back.

Breathtaking Bay Views!
I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

Auburn Roots Getaways Bunkhouse
I found the house very comfortable, a home away from home, with everything I needed. it was very clean and neat. While there are 2 other houses under construction on the road and one that seems to be a part time residence, the area is very quiet. I walked my dog along Rt 219 East and found a post office, church and an eclectic general store with snacks. coffee and used items for sale. All the activities I wanted to do were within 30 minutes to an hour away with my favorite in Bethel of the Wheeler Mica Mine tour and the Maine Gem and Mineral Museum. The Highland Grille at the golf course has fantastic food!
Quick stats about holiday rentals that are pet-friendly in Winthrop
Total rentals
20 properties
Nightly prices starting at
$77 SGD before taxes and fees
Total number of reviews
920 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- East End Beach
- Belgrade Lakes Golf Club
- Cliff House Beach
- Pemaquid Point Lighthouse
- Sunday River Golf Club
- Portland Museum of Art
- Maine Maritime Museum
- Portland Country Club
- Bradbury Mountain State Park
- Rockland Breakwater Light
- Wolfe's Neck Woods State Park
- Eaton Mountain Ski Resort
- Pinnacle Park
- Lost Valley Ski Area
- Head Beach
- Pebbly Beach