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Cottage vacation rentals in Windham

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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, 30 reviews

Charming Quiet Cottage close to hiking & JXN Falls

AaronRating, 5 stars3 weeks ago
Our stay at Chelsea and Mathew’s cottage was top notch. The communication and instructions on all things related to the cottage were detailed and clear. From prior to booking and throughout the stay the communication was excellent. The house was clean and well kept, charming and welcoming. The bonus features of the wood burning stove and hot tub made this a must stay location for us and we couldn’t have been happier with what they added to the overall experience. I highly recommend the spot for its proximity to Black Mountain, what the house offers and the hosts were fantastic. We’ll be back for sure!
Superhost
The cottage exterior features a white facade with blue trim and a welcoming entrance. Two Adirondack chairs are positioned on the front porch, surrounded by colorful flowers and greenery. A clear blue sky enhances the inviting look of this cozy retreat.
Cottage in Wells
4.89 out of 5 average rating, 57 reviews

Cozy beach cottage with pool & hot tub

PeggyRating, 5 stars8 months ago
Lovely one night stay at this sweet little cottage! Grounds are well-kept, enjoyed morning coffee on the front porch. AC kept it nice and cool. Convenient location close to a great donut shop- Congdon’s and our favorite ice scream spot- Scoop Deck. Chloe is a gracious host and even granted us a late check-out!
Top guest favorite
An aerial view of a two-story cottage reveals a welcoming exterior surrounded by greenery. A patio with outdoor furniture and an umbrella is visible on the side, while a hot tub and pool can be seen in the background, framed by colorful autumn foliage.
Cottage in Shapleigh
5 out of 5 average rating, 8 reviews

Lakeside Cozy Cottage in Nature | Hot Tub

NickRating, 5 stars1 week ago
This trip was more than we could've ever wanted! The property was lovely and the hosts were more than accommodating and made sure everything was as comfortable as it could've been! I'd recommend anyone to book with these hosts and I will definitely be booking again!
Superhost
A private hot tub rests on a wooden deck surrounded by lush greenery, providing a serene atmosphere. A small shed with a red door is visible in the background, framed by tall trees, creating a secluded outdoor space.
Cottage in Gilmanton
4.84 out of 5 average rating, 93 reviews

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

RomaRating, 5 stars2 weeks ago
Absolutely enjoyed our stay. Will definitely visit again in the future. The hot tub was very relaxing and was the highlight of our trip.
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
4.89 out of 5 average rating, 19 reviews

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

ChristinaRating, 5 stars1 week ago
We had a great stay at Audrey & Seb's place. It was spacious, beautifully decorated, and extremely clean. The beds were super comfortable, the location was private and close to town, and there was so much thought put into all the little details. What an absolutely wonderful place. Thank you so much!
Superhost
The exterior of a contemporary cottage is presented, featuring a light gray siding with dark blue shutters adorning the large front window. The entrance includes a wooden step leading to a dark front door, surrounded by a small patch of green plants.
Cottage in Wells
4.74 out of 5 average rating, 19 reviews

Contemporary Cottage With Ocean View 13

MiekaRating, 5 stars10 months ago
Terrific stay! The cottage was modern, clean, convenient and lovely. The pools are great for kids, and the cottage is near to restaurants, beaches etc. Great place for a holiday.
Guest favorite
A private cottage is set among lush greenery, featuring a sloped lawn that leads to the water. Purple chairs are positioned on the grass, inviting relaxation. The cottage boasts a peaked roof and large front windows, allowing for views of the surrounding nature.
Cottage in Sumner
4.95 out of 5 average rating, 19 reviews

Peace at the Pond with Hot Tub & Sauna

JimRating, 5 stars6 months ago
Wonderful,private, well equipped cottage on pretty pond. Owners quick to respond to our texts. Relaxing hot tub and fantastic sauna! Many restaurants and breweries within a 30 minute drive. Book it ..... you won't wanna leave!
Top guest favorite
A hot tub is situated on a wooden platform in the outdoor space, featuring a protective cover propped open. Steps lead up to the tub, which is filled with bubbling water. Surrounding the area are gravel and trimmed grass, providing a serene setting.
Cottage in York
4.98 out of 5 average rating, 189 reviews

Adorable cottage by Shorts Sands Beach

MikaylaRating, 5 stars1 week ago
Above and beyond in every way! Everything was extremely clean, easy to access, and very dog friendly. The host was incredibly responsive, flexible, and kind! We plan to go back!

Pet-friendly cottage rentals

Superhost
A wooden dock extends into the vibrant fall-colored landscape, leading towards a charming house with large windows. A rowboat rests gently on the water's edge, while colorful kayaks are lined up beside it. Comfortable seating is arranged on the lawn, inviting relaxation.
Cottage in Shapleigh
4.75 out of 5 average rating, 8 reviews

Relax at this Pet Friendly, Lakefront Getaway

JamieRating, 5 stars7 months ago
This was a great get away. Right on the lake with the convenience of using their kayaks, row boat, and peddleboat. Also had an array of life jackets for everyone to be safe. Scenery is beautiful, location is peaceful! We read, kayaked, played pinpong in their basement, sat around the firepit and listened to nature! The house is exactly how you see it in the pics, plus better! The home is spotless and has everything you need! Host Heidi is very responsive! They even have many board games and puzzles to play. I would highly recommend this property and plan to rent again. Thank you Heidi for sharing your home and for a lovely weekend. Jamie Hale
Top guest favorite
Two adirondack chairs, one red and one teal, are positioned on a sandy area overlooking a calm lake. Lush greenery surrounds the space, with small shrubs and trees framing the water view. The scene conveys a serene and inviting outdoor setting.
Cottage in Middleton
4.99 out of 5 average rating, 101 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

StefanieRating, 5 stars7 months ago
Another wonderfully relaxing stay! We really enjoyed the new screened in porch for morning coffee, late afternoon snacks, and evening games. The rainy days were just as lovely as the beautiful ones. We enjoyed the cozy gas stove on the cooler days, and we just couldn't have been more delighted by the welcome note and gift upon our arrival.
Top guest favorite
The cottage is situated on a hill, surrounded by lush green trees, and overlooks a tranquil bay. Rocky outcrops partially submerged in water are visible in the foreground, with a clear blue sky above enhancing the serene setting.
Cottage in Georgetown
4.98 out of 5 average rating, 117 reviews

Cottage on Todd Bay

MatthewRating, 5 stars6 months ago
Our group of 4 had a wonderful stay here. It had everything we needed and John was extremely helpful. We cooked several meals and visited nearby attractions.
Guest favorite
The exterior of the cottage is visible, featuring a welcoming front deck with white wicker seating. A small outdoor table with black wrought iron chairs sits on the grass, surrounded by trees, with two brick chimneys prominently displayed.
Cottage in Falmouth
4.97 out of 5 average rating, 73 reviews

Osprey Cottage, peaceful setting, walk to beach

MargaretRating, 5 stars6 months ago
Elizabeth was a wonderful host and her home is perfect for a peaceful, relaxing vacation. The house was spotless, well appointed, and very cozy. The short walk to the beach and town market is really convenient. Her rental is a perfect home base if you’re visiting Portland or exploring the Maine coast nearby.
Guest favorite
A private courtyard is featured, featuring gravel paths and bordered by white fencing. Adirondack chairs are arranged around fire pits, complemented by vibrant flower beds and planters. A shaded canopy and swings provide additional seating and leisure areas.
Cottage in Wolfeboro
4.93 out of 5 average rating, 41 reviews

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom

VincentRating, 5 stars2 weeks ago
Good place to stay lots of beds in a small footprint. Burners on the stove never got hot enough for me to cook my dinner or boil more than a cup of water but other than that everything worked great and check in and out was painless.
Guest favorite
A serene lakeside setting features three green adirondack chairs arranged around a stone fire pit. The clear waters of Great Pond reflect the blue sky, while a wooden dock extends into the lake, bordered by lush green trees in the background.
Cottage in Belgrade
4.93 out of 5 average rating, 135 reviews

Near Waterville | Lake Great Pond | Dog Friendly

TammyRating, 5 stars3 days ago
The place was beautiful and exactly what we needed! I would definitely recommend staying here.
Guest favorite
A wooden staircase leads down to a serene waterfront area, surrounded by lush greenery and trees. The calm water reflects sunlight, creating a shimmering path across its surface. A deck extends into the water, offering a peaceful spot to enjoy the view.
Cottage in Woolwich
4.92 out of 5 average rating, 178 reviews

Pet Friendly Audubon Bring Your Fishing Gear!

JulieRating, 5 stars6 months ago
What an amazing setting! Right on the water. We saw seals, osprey, and, we think, an eagle.Also the most beautiful sunrise. The house is cozy and comfortable and really really clean. We found everything we needed and some thoughtful extras. Tamara is an excellent host!
Guest favorite
A traditional two-story cottage features shingle siding and a gabled roof. The front entrance is framed by three large windows, with a set of steps leading to a well-maintained lawn surrounded by shrubs and flowers. A blue sky with scattered clouds provides a bright backdrop.
Cottage in York
4.9 out of 5 average rating, 117 reviews

Cozy Cottage by the Sea

KristinRating, 5 stars1 week ago
A large, comfortable home with the ocean in sight! The beach was stunning and the area was so quiet and peaceful in the off-season. Some great restaurants and shops were still open too. We’d love to return one day.

Private cottage rentals

Superhost
Cottage in Windham
4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

Jo-AnnRating, 5 stars7 months ago
This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.
Top guest favorite
A charming stone cottage stands beside a sandy beach, adorned with string lights that create a cozy glow. Two kayaks rest on the shallow water, reflecting the shoreline and lush trees surrounding the property.
Cottage in Falmouth
5 out of 5 average rating, 42 reviews

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug

MairaRating, 5 stars5 months ago
My husband and I spent 6 days here for our anniversary. I wanted a location on the water and close to visit all the major coastal towns in Maine. This was perfect! The home, felt like home, and everything was clean and beautiful. Adam was very helpful whenever I had any questions. Sipping coffee every morning on the back porch and watching the sunrise over the lake was so peaceful. Grocery store close by and great hiking/walking areas right out the front door. Can’t wait to come back and bring the family.
Guest favorite
A snow-covered pathway leads from a sandy beach to a serene ocean view. Frosted grasses frame the trail, contrasting with the smooth white snow. The clear blue sky reflects over the water, creating a sense of calm and tranquility in the scene.
Cottage in Scarborough
4.88 out of 5 average rating, 41 reviews

Cheerful 1 Bedroom Cottage Steps From The Ocean

BraulioRating, 5 stars1 week ago
Wonderful place clean and very cozy house I indicate
Top guest favorite
A scenic view of the lake is captured, showcasing vibrant autumn foliage on the opposite shore. Two red docks extend into the water, with a boat visible in motion. A picnic table and chairs are positioned on the grassy area adjacent to the docks.
Cottage in Alton
4.89 out of 5 average rating, 61 reviews

Lake view cottage #1 in Alton Bay on Winnipesaukee

JustinRating, 5 stars6 months ago
Janet, was an amazing host, super helpful with answering any questions we had. Also was helpful in assisting when we arrived later in the evening. The cottage is beautiful and right on the lake with an amazing view. Close by to all the towns around the lake it’s the perfect location. It was super clean and cozy and a great spot to stay for a trip to NH.
Top guest favorite
Cottage in Standish
4.97 out of 5 average rating, 61 reviews

Big Sebago Lake Rentals Waterfront w Private Beach

AndreaRating, 5 stars6 months ago
Beautiful location, perfect stay with amazing hosts! This was the perfect getaway for our family and we cannot wait to go back! The location can't be beat and Kate and Barry went above and beyond to make sure we had everything we needed. Highly recommend!
Superhost
A clear blue swimming pool reflects the sunlight, surrounded by lounge chairs. Umbrella shades are positioned nearby, providing options for relaxation. Trees line the area, enhancing the natural setting against a bright sky filled with clouds.
Cottage in Poland
4.75 out of 5 average rating, 20 reviews

Alvan Riccar Cottage 3 at Poland Spring Resort

ChelseyRating, 5 stars32 months ago
Loved it! It was relaxing and deff worth the price. We’ll deff be back next time we’re in the area.
Superhost
A sandy beach scene is presented, featuring smooth rocks along the shoreline. Gentle waves meet the sand, while a distant row of beach houses is visible under a clear blue sky. Two individuals can be seen walking along the water's edge.
Cottage in Wells
4.78 out of 5 average rating, 9 reviews

Seaside Escape

AngelikaRating, 5 stars7 months ago
The location was amazing. Just a few steps to Crescent Beach. I actually took my coffee down there and watched the sunrise in the morning. So beautiful. The cottage was clean and comfortable. Kristin was very responsive and helpful. Don't miss out on the clam chowder at the Lobster Pound less than 100 meters away. We'd definitely come again.
Superhost
An indoor swimming pool is visible, featuring clear blue water and well-maintained surroundings. Natural light enters through large windows, illuminating the space. Safety signs indicate a cautionary note, while potted plants add a touch of greenery to the inviting environment.
Cottage in Saco
4.9 out of 5 average rating, 10 reviews

Saco Cozy Cottage! Minutes From Old Orchard Beach

NancyRating, 5 stars6 months ago
The cottage was perfect for our needs and had everything! Auria was extremely helpful and responded to us quickly! I would definitely stay there again!

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