
Cottage vacation rentals in Windham
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Top-rated cottage rentals in Windham
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windham cottage rentals
Cottage rentals with a hot tub

Charming Quiet Cottage close to hiking & JXN Falls
Truly magical stay at Chelsey’s place. Perfect spot for unwinding after a day adventuring the White Mountains. Would stay again!

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront
A great spot tucked away!! House was cute and as shown in the pictures, is right on the water and has some great views! It rained the majority of the time we were there so didn’t get to take advantage of all the outdoor amenities, but would have if better weather! Host was very friendly, communicative and responsive!

Fully Renovated/4min to K-port/HotTub/Game Room
Great clean air bnb. Accurately as described.. looks good in photos but even better in-person. Bed was comfortable. Would rent their properties again.

Waterfront Getaway w/ Private Sandy Beach
Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.

The Loon Nest, Waterfront Lake House, Wood Hot Tub
The house was clean and well maintained. The view was gorgeous, too bad Mother Nature didn’t cooperate. It was cold and rainy. Used the fire pit nightly and it was nice. Linens were clean, towels were soft and fluffy and smelled freshly laundered. Kitchen was spotless and well stocked with pot/pans and dishes. Having a dishwasher was nice too. Two grocery stores (Hannaford and Market Basket) were close by and plenty of restaurants too. We came with the intention of doing nothing and just changing scenery for the weekend. This place was perfect.

Cottage in Wells Maine
We had a wonderful stay here and highly recommend it! The location is great, as it’s close to plenty of restaurants and stores. We were even able to walk to get breakfast and dinner. The space itself was much larger than we expected and very clean. The kitchen had everything we needed and we even had snacks, waters, and coffee left for us! The highlight for my 2 year old was the pirate ship playground. We also loved having access to picnic tables. We got takeout and enjoyed eating outdoors. We did not use the outside grill but that is a great addition and we would have used if we stayed longer. The host was very helpful and accommodating. They offered early check in and check out and gave very clear instructions on how to get in. I would not hesitate to return in the future!

Adorable cottage by Shorts Sands Beach
Camille’s place is fantastic! Great location and it’s so clean and well decorated. Camille is so fast to communicate and is very accommodating. We’ve stayed many times and look forward to returning again.

Cozy Cottage with Ocean Views, Wells Maine
The cottage is spotless, well-stocked and conveniently located for day trips in any direction. This is our 4th year staying at this lovely cottage for a pre-holidays getaway. We look forward to keeping this annual tradition!
Pet-friendly cottage rentals

Cottage on Todd Bay
We had a great stay! The house is very nice with a view of the bay and the screened in porch was an great place to be outside but away from the bugs. The surroundings are peaceful and quiet and the house had everything we needed with appropriate notes in all the right places.

Tall Pines Hideaway
Beatiful cabin on the water, thoughtfully decorated. I loved the layout, plenty of seating areas and lovely decor. There is only one small bathroom which may be an issue with more than 2 or 3 guests, but worked out perfectly for us. We saw deer twice when driving down the trail to the house which was exciting! Loved using the firepit outside. The only bummer was that the dock wasn’t in the water yet. I still managed to use the kayak but would not advise attempting without the dock lol. Wonderful host, David was very responsive and had a nice bottle of wine waiting for us on our arrival. Would 100% come back

Pet Friendly Audubon Bring Your Fishing Gear!
Tammy describes her sweet cottage perfectly. Water views are spectacular with options to fish off the dock, sit in the backyard to warm up or sit on the bluff to cool off. It was perfect for this girl and her dog to re-set in solitude. Most places on the water have sensitive septic as described so you want to consider that if there are more than two guests. I enjoyed my endless walks on Popham beach (no dogs 4/1-10/1)) and was thrilled to be there in the off season. I barely saw anyone! Reid State Park was also spectacular and more opportunity to walk my dog on the trails. Tick season is a bit of an adjustment every year but not a problem if you prepare yourself and your furry friends. A perfect place for a great book, wandering around historic Bath, and easy meal prep. I stayed 2 weeks and appreciated all the thought Tammy put into anticipating what a traveler might need.

RK North : All season Waterfront cottage with dock
A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

Classic Lakefront Maine Cabin
What a beautiful location! David is a great host. He made sure we had good directions, tips for the area, and was quick to answer any questions. The lakeside cabin has absolutely everything you need to have a peaceful, relaxing vacation. The view of the lake is spectacular. The cabin is very clean, has a well stocked kitchen, comfortable beds and Echo lake is a gorgeous pristine lake. Every morning, we enjoyed our coffee on the dock. We swam, kayaked, canoed and even tried out the paddle boards that came with the house. We would love to come back! Thanks!

Hermit Thrush House
Barbara place is awesome for a couple plus I child nice quiet area very clean and it private. Barbara is a great host you will love this spot it feels like home we will be back

Waterscape Cottage - private waterfront
We loved staying at Ann's place! It was exactly what we wanted, close to town and to lots of activities but also felt remote and in a really gorgeous location. Great, rustic spot.

Lakefront, Beach Private, Amazing Views, & pets!
Helen was actually wonderful. She returned calls and everything. It was a great place to stay beautiful and hope to stay there again someday.
Private cottage rentals

The Purple House by Pettingill Pond
We cannot say enough good things about this place. We just felt so comfortable and "at home" here. The only things that we had to overcome were having only one bathroom (and it was on the bottom floor, whereas the two bedrooms with more than a twin bed were on the 2nd floor), and the narrow treads on the steps going up to the 2nd floor. I was afraid I would fall down them more than once. But none of these things detracts much from the overall value and feel of the property. And they are certainly not the host's fault. We managed just fine. The small things were what set this place apart from others we've stayed at. Lots of little details are added to make the overall stay more comfortable. I won't list them all here; you just need to see it to believe it. We will most definitely stay here (if it's available) on our next trip to Windham!

The Lil'house - A Mountain Top Modern Cottage
Dan and Jane have a beautiful home. They were extremely kind and I can’t thank them enough for allowing me and the kids to meet their horses. It is a wonderful property on a serene landscape. The pictures don’t do it justice. We will certainly be back.

Coastal Waterfront Tiny home in West Bath
What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!

Covered Bridge Cottage - Maine woods and river
Had an extremely great time. Everything was as listed in the rental,easy accessibility to kayaks,river,grill,fire pit,and the host ( Laura)was only a text away if needed. House was spotless and had Everything needed to enjoy a get away. Price was definitely worth it,and we would not hesitate to book again. Two thumbs up and 5 stars to Laura and all involved in the rental,very well managed and maintained.

Sebago Lake, the way life should be: lake cottage
Better than we ever could’ve imagined! We stayed for 2 nights in October: the cabin was perfect, the lake was beautiful, and they had provided everything we could’ve possibly needed in terms of amenities. Highly recommend lighting up a fire in the fireplace and taking a quiet evening to watch the sunset over the lake from the comfy living room couch! We will definitely be back.

Secluded Coastal Home & Cottage 3 Minutes to Beach
Our stay at Thistle Pond Cottage was incredible! Alexis and Hamish have really designed a space to make you feel right at home. The kitchen was seriously amazing, so many great touches and the bedrooms and bathrooms are INCREDIBLE. The shower was one of the best I’ve ever taken, hahah. Not to mention the nature of the surrounding property! The cherry on top was daily visits from Alexis and Hamish’s sweet Great Dane, Leah!! I brought my 14mo old son on vacation with us and it was the PERFECT place for him, he loved it. We felt right at home and would love to come back!! P.S. the homemade sourdough was some of the best I’ve ever had!! We loved Maine and our stay at the cottage. Highly recommend, especially for travel with babies!

Lovely Lakefront Cottage - Book Your Fall GetAway!
Wow what a spot!!! Kristen thought of everything to make our family’s stay so comfortable. Tastefully decorated. Amenities abound. Spotless! It was so peaceful having morning coffee or relaxing around the campfire with the gorgeous backdrop of Panther Pond and the symphony of the loons. Kristen is a highly responsive host who wants your stay to be perfect. Communication was excellent. We cannot recommend this hidden gem more highly!

Beautiful Maine Lakefront Cottage
This place was great! Private and beautiful. no need to leave if you don't want too. kayaks, fishing, outdoor fire and sitting, indoor games. inside had everything you need or want for a week of peace, quiet, and fun!
Quick stats about cottage rentals in Windham
Total rentals
30 properties
Nightly prices starting at
G$18,823 GYD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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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