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

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More
We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

Hilltop Retreat with Hot Tub & Sauna near Downtown
Everything was as described and more! With a wonderful location close to town, good privacy, and so much space inside with many commodities we wouldn’t even think of. Even our dog had a fun filled week with us. We hope to visit again, it’s just the perfect home away from home. Couldn’t recommend a better place to stay.

Stone Isle. 8 acres next 2 little john preserve.
Jeffrey’s guest house is super special, it was amazing to be able to look out every window to experience coastal Maine and so serene and peaceful. Located on a beautiful property right on the bay in a wooded setting. Very private and quiet. We absolutely loved our stay - in fact we extended it another 3 days to be able to enjoy it longer. Jeffrey was very accommodating and even credited us for the 2nd cleaning fee charged by Airbnb because we needed to change our payment method for the extended stay. I can’t say enough about the comfy bed!! I felt like I was sleeping in a cloud with super soft sheets and perfect mattress. I wish all Airbnb hosts were as thoughtful about the personal touches as Jeffrey. I had to work a bit during the trip and the internet was very stable and easy to connect to. It was a perfect retreat for us. Highly recommend staying here! We will. Definitely will Return!

Cozy Guest Suite in White Mountain National Forest
Mary's place was great. Everything was exactly as described and Mary gave very clear instructions for check in and responded quickly to text messages. It was a very enjoyable stay.

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!

Lakehouse on Highland Lake
Beautiful place in great location. Did a weekend trip that included Portland based activities and a lake day at Lake Sebago. This was right in between making both super easy! The house was beautiful, clean, and slept everyone very comfortably. The view on the water is amazing, and Timissa was very responsive, accommodating, and kind!

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.

The Hendrick House
It has been a wonderful experience getting to meet and work with this couple! Very understanding and accommodating and beautiful home and location I highly recommend!
Pet-friendly home rentals with a pool

Storyland, golf, hiking, kayak and more
We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

Spacious Condo-Attitash Ski-Storyland-Saco & More!
Beautiful place to stay! Great amenities for the kids ! Will definitely go back ❤️

Cozy Top Floor-1 King, Mtn View, Jetted Tub, Pools
The place was so clean, quiet and peaceful. Secluded but so much to do in a short area. Can’t say enough good things. Will be coming back.

"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!

Bartlett N. Conway, NH condo ski near Storyland
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

An Amazing Mountain Getaway!
My family and I had an amazing weekend. Melissa was very responsive and flexible with checking in/out. Everything was clean, plenty of linens and towels, great location, comfy beds. 10/10. We can’t wait to be back!

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.

OOB Oasis - 5BR private Retreat w/ Pool
Great house! Very spacious, plenty of bathrooms, and fantastic location. Very easy to communicate with the owners and check in/out was simple. My minor only critique is that we wish the grill were a bit bigger and nicer. We wanted to grill one day, but we were a little disappointed and unable to do so due to the grill quality. Would definitely stay again!
Private, pet-friendly home rentals

Suburban Studio Apt in a quiet family neighborhood
This lovely property was perfect for us. The host really knows how to “think like a guest” and has anticipated what will make you feel comfortable and at home with numerous little extras. The apartment is beautifully decorated and the bed and furniture were comfortable. Will definitely book on our next visit.

Serenity between the lakes & sea
We had an excellent stay at David's place. It was exactly what my family and I needed and the location was perfect. We will definitely stay there again.

Cozy In Law Suite Fully Equipped
We had a very relaxing stay at Carl & Rose's place. It was a very cozy space on a rainy fall weekend. Lots of fleece blankets, pillows and tea made us feel warm and welcome. The oversized reclining couch and 4-poster bed were super comfy. The height of the bed was a bit intimidating at first but quite luxurious once you sink into the soft supportive mattress. Great home base for exploring the beautiful scenery of Maine and nearby NH, especially with the leaves in full color.

Romantic Hidden Cottage!
Misty’s cabin was very cute, cozy, and private. We loved soaking in the hot tub and listening to the frogs and crickets at night! The bed is kind of firm and springy but was doable for a short stay. Would definitely recommend grabbing breakfast at the cafe 1055 across the street, we ended up stopping there twice and it was delicious both times. Misty had great communication during our stay as well!

Classic Maine Cabin, Private Waterfront, Fireplace
Staying at Braden's camp cabin was great! We enjoyed using the indoor wood-burning fireplace and sitting out on the porch. It was colder this weekend than we anticipated, but the heating worked well in the bunk house and we were able to stay cozy. Would recommend staying here for a simple, no-frills kind of experience.

Cozy cabin on the lake with the loons
This cabin is one of the most wonderful places I have been. My partner and I stayed just under a week and we enjoyed every second! It was so peaceful and relaxing to be away in such a beautiful home in an amazing area!

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.

Cozy Camp on the lake
The time that I spent at Julie’s camp was amazing! It was even better than described! Julie thought of everything from sharing restaurants and things to do; an awesome multi-device charging station; and even a welcome snack basket and bottle of wine. My pup, Gracie, had a great time as well scouting all the waterfowl on the lake and just having some good country fun. I hope to get back to Julie’s amazing camp at the end of the summer. It’s a real gem as is the host, Julie.
Quick stats about vacation rentals that are pet-friendly in Windham
Total rentals
60 properties
Nightly prices starting at
G$16,732 GYD before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
50 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Story Land
- Attitash Mountain Resort
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cranmore Mountain Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths