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Cottage vacation rentals in Windham

Find and book unique cottages on Airbnb

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Popular amenities for Windham cottage rentals

Cottage rentals with a hot tub

Guest favorite
The cottage is surrounded by a lush landscape, featuring a natural stone wall and steps leading to the entrance. Tall trees and scattered foliage provide a backdrop that complements the earthy tones of the wood exterior. A chimney is visible on the side, suggesting a cozy interior.
Cottage in Jackson
5 out of 5 average rating, 31 reviews

Charming Quiet Cottage close to hiking & JXN Falls

JohnRating, 5 stars1 month ago
Truly magical stay at Chelsey’s place. Perfect spot for unwinding after a day adventuring the White Mountains. Would stay again!
Superhost
A serene lakeside scene showcases a wooden dock extending into the water, surrounded by lush trees. Two kayaks and a canoe are positioned on the shore, while the sunset casts a warm glow on the lake's surface, reflecting vibrant hues of orange and pink.
Cottage in Limerick
4.78 out of 5 average rating, 68 reviews

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront

ShannonRating, 5 stars1 week ago
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!
Superhost
The living area features a brown leather sofa paired with a decorative throw, surrounded by large windows that invite natural light. A textured area rug lies beneath a low coffee table, with decorative objects and plants adding a touch of greenery.
Cottage in Gilmanton
4.85 out of 5 average rating, 101 reviews

Hot Tub - Walk to the Beach - Mins to Mtns - Lakes

YannRating, 5 stars3 weeks ago
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!
Guest favorite
A bright living area features a comfortable gray sofa adorned with patterned cushions, complemented by a cozy teal accent chair. A round wooden coffee table sits in front, surrounded by a light area rug. Bookshelves and decorative elements enhance the inviting ambiance.
Cottage in Kennebunk
4.92 out of 5 average rating, 25 reviews

Fully Renovated/4min to K-port/HotTub/Game Room

Maverick & MichelleRating, 5 stars3 weeks ago
Great clean air bnb. Accurately as described.. looks good in photos but even better in-person. Bed was comfortable. Would rent their properties again.
Superhost
A comfortable outdoor space is presented with a grassy area surrounded by trees. Blue chairs are arranged around a fire pit, and large windows of the two-story home reflect the natural light. A sense of privacy is offered by the surrounding foliage.
Cottage in Casco
4.88 out of 5 average rating, 24 reviews

Waterfront Getaway w/ Private Sandy Beach

RileyRating, 5 stars1 month ago
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.
Guest favorite
A screened-in porch features a sectional sofa surrounding a glass-top table, providing a comfortable seating area. Large windows offer views of the surrounding trees, allowing natural light to fill the space. A fireplace adds a focal point, enhancing the cozy retreat atmosphere.
Cottage in Northwood
4.96 out of 5 average rating, 101 reviews

The Loon Nest, Waterfront Lake House, Wood Hot Tub

ChristinRating, 5 stars3 weeks ago
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.
Guest favorite
The exterior of the studio is shown, featuring a main entrance with large windows that provide natural light. A charcoal grill is positioned nearby, along with two blue adirondack chairs on a simple porch. The area is surrounded by gravel and concrete, with green grass visible in the background.
Cottage in Wells
4.93 out of 5 average rating, 45 reviews

Cottage in Wells Maine

DavidRating, 5 stars3 days ago
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.
Top guest favorite
An open-concept living area is showcased with a light wooden ceiling and modern decor. Comfortable seating is arranged around a coffee table, with a dining table visible in the background. A lofted area and kitchen appliances complete the well-lit space.
Cottage in Cape Neddick
4.98 out of 5 average rating, 197 reviews

Adorable cottage by Shorts Sands Beach

KatieRating, 5 stars1 week ago
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

Superhost
A cozy beach house is set within a spacious backyard featuring a wooden deck. A circular fire pit area is surrounded by several chairs, while lush green grass and colorful flowers enhance the outdoor setting. The house is adorned with a simple 'BEACH HOUSE' sign.
Cottage in Old Orchard Beach
4.93 out of 5 average rating, 309 reviews

#1 Cozy cottage minutes from the beach!

EmilyRating, 5 stars2 weeks ago
We had a great stay for a few days on our way to Nova Scotia. Cottage was clean and had everything we needed.
Top guest favorite
A deck overlooking the water features a round table surrounded by four chairs, each with turquoise cushions. An umbrella stands in the center of the table, providing shade. A decorative rug with an oceanic design is positioned underneath the table, complementing the serene water views.
Cottage in Eliot
4.99 out of 5 average rating, 148 reviews

Salty Mermaid Cottage/Boat House

GaryRating, 5 stars2 weeks ago
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.
Top guest favorite
A cottage is nestled along a winding road, surrounded by vibrant fall foliage. Warm hues of orange, red, and yellow adorn the trees, contrasting against the clear blue sky. A grassy area and a few stones are visible in the foreground, providing a welcoming entrance to the property.
Cottage in Georgetown
4.98 out of 5 average rating, 121 reviews

Cottage on Todd Bay

KuenziRating, 5 stars1 week ago
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.
Guest favorite
A cozy outdoor seating area is set up on a gravel surface, featuring two wooden lounge chairs and a small table under a white umbrella. The blue exterior of the guest house is visible in the background, with steps leading to the entrance.
Cottage in Saco
4.94 out of 5 average rating, 423 reviews

Deja Blue~Guest Beach House

ChrisRating, 5 stars6 days ago
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!
Top guest favorite
Tall trees frame a serene pond, with calm waters reflecting the surrounding greenery. The landscape features gentle hills in the background, adding depth to the natural setting. Soft sunlight filters through the leaves, creating a peaceful ambiance by the water's edge.
Cottage in Waterford
4.99 out of 5 average rating, 145 reviews

Tall Pines Hideaway

JessRating, 5 stars1 week ago
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
Guest favorite
The serene view showcases a sunrise over the calm waters of the Sasanoa River, reflecting golden hues. Lush greenery frames the scene, while the distant treeline adds depth to the landscape. Soft clouds linger above, enhancing the tranquil atmosphere of the setting.
Cottage in Woolwich
4.92 out of 5 average rating, 182 reviews

Pet Friendly Audubon Bring Your Fishing Gear!

LisaRating, 5 stars1 week ago
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.
Guest favorite
A tranquil lakeside scene captures a small dock with a chair and table set under the warm glow of sunset. Surrounding greenery frames the view, enhancing the serene atmosphere of the water, which reflects the soft hues of the evening sky.
Cottage in Fayette
4.97 out of 5 average rating, 101 reviews

Classic Lakefront Maine Cabin

CarolRating, 5 stars9 months ago
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!
Top guest favorite
A charming cottage is surrounded by greenery, featuring large windows that allow natural light to enter. Two red Adirondack chairs are positioned in front, offering a cozy spot to relax. A small stone stack adds a touch of nature to the landscape, which is dotted with grasses and trees.
Cottage in Kittery Point
4.95 out of 5 average rating, 158 reviews

Cozy Maine Cottage by the Sea

LinaRating, 5 stars3 days ago
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

Guest favorite
A serene view of the calm lake stretches towards the horizon, framed by lush greenery and a clear blue sky. A wooden dock extends into the water, accompanied by two chairs positioned for tranquil seating, inviting moments of relaxation and contemplation.
Cottage in Raymond
4.96 out of 5 average rating, 46 reviews

Relaxing New England Lakeside Getaway

GuyRating, 5 stars1 week ago
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!!!
Top guest favorite
Cottage in Falmouth
5 out of 5 average rating, 44 reviews

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug

ZephyrRating, 5 stars1 week ago
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!
Guest favorite
A bright dining area features a circular table surrounded by two gray chairs, with a decorative pillow on one. A leafy plant is positioned next to the sliding glass doors, allowing natural light to fill the space, complemented by light-colored wood floors and a patterned rug.
Cottage in Windham
4.87 out of 5 average rating, 69 reviews

The Purple House by Pettingill Pond

ShanlynnRating, 5 stars1 month ago
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!
Top guest favorite
A covered porch features two wicker chairs and a small table. The wood surface extends outward, leading to scenic views of distant mountains and open landscapes. Warm sunlight enhances the inviting atmosphere of this outdoor space.
Cottage in Cornish
5 out of 5 average rating, 70 reviews

The Lil'house - A Mountain Top Modern Cottage

DanielleRating, 5 stars2 days ago
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!
Guest favorite
Two green Adirondack chairs are positioned by the water's edge, facing a serene and reflective pond. Surrounding trees showcase a variety of autumn colors, enhancing the tranquil atmosphere of the wooded environment.
Cottage in Windham
4.9 out of 5 average rating, 79 reviews

Covered Bridge Cottage - Maine woods and river

KeithRating, 5 stars3 weeks ago
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.
Superhost
A charming cabin sits nestled among tall trees, featuring a blend of white and green siding. The tranquil lake is visible in the background, complemented by a sunny blue sky. The property showcases a peaceful outdoor setting, ideal for relaxation by the water.
Cottage in Windham
4.73 out of 5 average rating, 64 reviews

Sebago Lake, the way life should be: lake cottage

CharlieRating, 5 stars8 months ago
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.
Top guest favorite
Cottage in Raymond
5 out of 5 average rating, 84 reviews

Lovely Lakefront Cottage - Book Your Fall GetAway!

LeslieRating, 5 stars3 weeks ago
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!
Guest favorite
Cottage in Sebago
5 out of 5 average rating, 22 reviews

Sebago Lake waterfront Cottage

CharlieRating, 5 stars3 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Windham
  6. Cottage rentals