
Cottage vacation rentals in Windham
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Top-rated cottage rentals in Windham
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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!

Hot Tub - Walk to the Beach - Mins to Mtns - Lakes
I had a nice stay at Alexa's. It's beautiful, quiet and ideal to get some rest while being surronded with nature. The best!

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
Great cottage with a perfect location. Not too close to the ocean but close enough. Grocery stores and other shops within a mile radius. 10-20 miles gets you to many other small Maine locations.

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.
Pet-friendly cottage rentals

#1 Cozy cottage minutes from the beach!
We had a great stay for a few days on our way to Nova Scotia. Cottage was clean and had everything we needed.

Salty Mermaid Cottage/Boat House
My family and I loved Skye's place. It was very private with a great view of the river and a nice sunset. Lots of different sea birds including a family of geese that had just hatched. Skye's place was very well equipped with all the little conveniences we would normally supply ourselves from coffee and creamer to ice in the freezer. The location was perfect for us, because the focus of our trip was shopping. Less than ten minutes from the outlet stores We would definitely stay there again when in the area.

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.

Deja Blue~Guest Beach House
micheles place was incredibly well stocked with helpful and cute amenities and convenience items! the view and accessibility to the beach is incredible. Michele was very welcoming and we appreciated all of the recommendations she provided. the guest house is quite small but met my and my husband's needs for a quick getaway. thank you for your hospitality!

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.

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!

Cozy Maine Cottage by the Sea
This is our third time at this cottage. I presume it says it all! thank you so much! The place is extremely cozy and spotless.
Private cottage rentals

Relaxing New England Lakeside Getaway
What a fantastic cabin! Just the right size for two friends to share for a long weekend in SW Maine. Christopher's Oxbow Brewery food recommendation was spot-on, our favorite meal of the whole trip! The water was calm and tranquil just like the surroundings, and the loon calls were out of this world. I would definitely stay here again!!!

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
Great cottage right on the lake! Kayaks were great to take out and explore the lake and see wildlife as well. The cottage is spacious and comfortable. The kitchen is large and well appointed for any cooking you may want to do. Grill and plenty of beach chair/ towels available as well. Adam is extremely responsive and I highly recommend. The place is quite peaceful though the lake gets pretty busy on the weekends with boats but not in an obnoxious way. Loved sipping coffee and reading on the dock each morning. Will definitely book again!

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
We absolutely loved our stay at Jane & Dan’s house. It was perfect. We felt so peaceful and relaxed during our time there. We thoroughly enjoyed sitting outside on the porch swing while the sun was setting watching the mountains, horses and sunset. Can’t wait to come back!

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.

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!

Sebago Lake waterfront Cottage
Overall, it was a great experience! Very peaceful and on a private road. I appreciated a clean and welcoming place! I would recommend this spot and stay here again. Owner was very kind and responded to any questions I had. Only thing that could improve was the kitchen layout. Kitchen iteam were in odd locations. I had to open each cabinet to find the oven mitts. This is a very little critique, and I would still rate it five out of five stars!
Quick stats about cottage rentals in Windham
Total rentals
30 properties
Nightly prices starting at
$90 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
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Long Sands Beach
- Attitash Mountain Resort
- Pemaquid Beach
- Diana's Baths
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Brunswick Golf Club
- Cliff House Beach
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Cranmore Mountain Resort
- Purity Spring Resort
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