Cottage holiday rentals in Windham

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Popular amenities for Windham cottage rentals

Cottage rentals with a hot tub

Guest favourite
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
Cottage in Limerick
4.78 out of 5 average rating, 68 reviews

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront

ShannonRating, 5 stars6 days 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!
Guest favourite
Cottage in Kennebunk
4.92 out of 5 average rating, 25 reviews

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

Maverick & MichelleRating, 5 stars2 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
Cottage in Casco
4.88 out of 5 average rating, 24 reviews

Waterfront Getaway w/ Private Sandy Beach

RileyRating, 5 stars3 weeks 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 favourite
Cottage in Northwood
4.96 out of 5 average rating, 101 reviews

The Loon Nest, Waterfront Lake House, Wood Hot Tub

ChristinRating, 5 stars2 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 favourite
Cottage in Wells
4.93 out of 5 average rating, 44 reviews

Cottage in Wells Maine

KaylaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Cottage in Cape Neddick
4.98 out of 5 average rating, 197 reviews

Adorable cottage by Shorts Sands Beach

KatieRating, 5 stars4 days 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.
Guest favourite
Cottage in Wells
4.94 out of 5 average rating, 148 reviews

Cozy Cottage with Ocean Views, Wells Maine

JanaRating, 5 stars6 months ago
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

Top Guest favourite
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.
Top Guest favourite
Cottage in Waterford
4.99 out of 5 average rating, 144 reviews

Tall Pines Hideaway

JessRating, 5 stars6 days 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 favourite
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.
Superhost
Cottage in Lyman
4.82 out of 5 average rating, 102 reviews

RK North : All season Waterfront cottage with dock

EricRating, 5 stars1 week ago
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
Guest favourite
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 favourite
Cottage in South Bristol
4.97 out of 5 average rating, 104 reviews

Hermit Thrush House

DemetriaRating, 5 stars2 days ago
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
Guest favourite
Cottage in Wiscasset
4.88 out of 5 average rating, 274 reviews

Waterscape Cottage - private waterfront

SophieRating, 5 stars1 week ago
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.
Superhost
Cottage in Freedom
4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Leigh AnnRating, 5 stars3 weeks ago
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

Guest favourite
Cottage in Windham
4.87 out of 5 average rating, 69 reviews

The Purple House by Pettingill Pond

ShanlynnRating, 5 stars3 weeks 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 favourite
Cottage in Cornish
5 out of 5 average rating, 69 reviews

The Lil'house - A Mountain Top Modern Cottage

MatthewRating, 5 stars7 months ago
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.
Top Guest favourite
Cottage in West Bath
4.92 out of 5 average rating, 77 reviews

Coastal Waterfront Tiny home in West Bath

LeahRating, 5 stars5 days ago
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!
Guest favourite
Cottage in Windham
4.9 out of 5 average rating, 79 reviews

Covered Bridge Cottage - Maine woods and river

KeithRating, 5 stars2 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
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 favourite
Cottage in Biddeford
5 out of 5 average rating, 33 reviews

Secluded Coastal Home & Cottage 3 Minutes to Beach

HayleyRating, 5 stars2 days ago
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!
Top Guest favourite
Cottage in Raymond
5 out of 5 average rating, 84 reviews

Lovely Lakefront Cottage - Book Your Fall GetAway!

LeslieRating, 5 stars2 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 favourite
Cottage in Poland
4.96 out of 5 average rating, 27 reviews

Beautiful Maine Lakefront Cottage

MonicaRating, 5 stars8 months ago
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

    $139 AUD 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