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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

Superhost
The front exterior of a single-story cottage is depicted, featuring light purple siding and large windows. Two red Adirondack chairs surround a small table on a grassy area, alongside a wooden pathway leading to the entrance, which is flanked by decorative plants.
Cottage in Wells
4.76 out of 5 average rating, 42 reviews

Cozy Cottage close to Beach, Pool and more!

JanelleRating, 5 stars7 months ago
Dear Tim and Kimberly - I wanted to express how much we enjoyed our stay at your delightful two-bedroom cottage. The accommodations were not only beautifully furnished but also incredibly comfortable. The added amenities, including the pool, hot tub, and gym, made our stay even more enjoyable, offering plenty of options for relaxation and fitness. We also loved how close the cottage was to the local restaurants and the beach—it was the perfect location for a relaxing getaway. Your attention to detail made all the difference, and we couldn't have asked for a better experience. I will definitely recommend your place to others and look forward to returning in the future! Janelle Q PS - I live in Florida and upon my return from Maine, am being greeted by Helene. JQ
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 stars2 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 stars7 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, 7 reviews

Lakeside Cozy Cottage in Nature | Hot Tub

NickRating, 5 stars4 days 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!
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 stars6 days 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!
Guest favorite
A modern kitchen features a sleek countertop with a variety of fresh ingredients arranged on plates. A coffee maker is visible in the background, alongside a stainless-steel kitchen appliance. Natural light enters through a window, illuminating the stylish grey and white color scheme.
Cottage in Wells
4.94 out of 5 average rating, 16 reviews

Beautifully renovated 2-bedroom cottage

LisaRating, 5 stars7 months ago
Everything was so perfect !! thank you for hosting us !!
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.
Superhost
A vintage cottage is showcased with a three-season porch featuring large windows. A picnic table is positioned on a grassy area, surrounded by garden beds. Two Adirondack chairs are placed nearby, inviting relaxation in a serene outdoor setting.
Cottage in Wells
4.88 out of 5 average rating, 32 reviews

Vintage Maine 2 Bedroom Cottage

AllisonRating, 5 stars7 months ago
Beautiful place to stay!! Quintessential Maine. We had a great experience, made use of the cabin, pool, and picnic area while in town for a wedding—and a much better value than places the next town over!!

Pet-friendly cottage rentals

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 stars5 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 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!
Top guest favorite
The serene lakeside view features a sandy beach area framed by trees. A picnic table and kayaks are positioned nearby, with a dock extending into the calm water. The clear sky reflects gently on Little Sebago Lake, creating a peaceful natural setting.
Cottage in Gray
4.9 out of 5 average rating, 209 reviews

Sunset Haven - Little Sebago Lake

MonicaRating, 5 stars3 days ago
Absolutely loved our stay at this lake cabin! It's nestled right on the water, making it a perfect spot for peaceful mornings and unbeatable fishing. The sunsets over the lake are absolutely stunning — a real highlight of the trip. The cabin itself has a rustic charm, filled with unique vintage touches that make it feel cozy and full of character. It's quiet, far enough from the city to truly relax, but still conveniently close to town if you need anything. A wonderful place to unwind and make lasting memories with family. Can't wait to come back!
Top guest favorite
Cottage in Bridgton
4.9 out of 5 average rating, 235 reviews

Rustic Pebble Cottage in beautiful Bridgton, Maine

CatherineRating, 5 stars6 days ago
Pebble Cottage was so peaceful yet close to everything. We kept ourselves quite busy locally and Cheryl's place was a perfect spot to unwind and relax at the end of a busy day. The host is a beautiful artist and an exceptional, sweet human being. We hope to return in the Fall. Thanks Cheryl!
Guest favorite
A wooden dock extends into Highland Lake, surrounded by calm waters. Lush greenery and trees frame the scene, with vibrant autumn colors reflected in the water. The shoreline features gentle grass and a few rocks, creating a serene lakeside atmosphere.
Cottage in Windham
4.93 out of 5 average rating, 106 reviews

Cozy Cottage on Highland Lake

MeredithRating, 5 stars6 months ago
Perfect little Maine cabin getaway! We enjoyed our stay so much. The cabin was clean, easy to find, and had everything we needed for four people and two dogs. Cannot recommend enough!
Guest favorite
The exterior of a charming cottage is shown during twilight, illuminated by warm lights. A large star adorns the peak, while the windows reveal a decorated Christmas tree and a cozy atmosphere. Festive decorations hang along the balcony and entrance.
Cottage in Harpswell
4.91 out of 5 average rating, 202 reviews

H and K Cove View Cottage LLC

MathieuRating, 5 stars3 months ago
Amazing place, and amazing host! This was our second time at Kristen’s and we’re definitely looking forward to going back.

Private cottage rentals

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 stars2 days ago
Wonderful place clean and very cozy house I indicate
Top guest favorite
A charming cottage is surrounded by lush greenery, with a spacious lawn and soft sunlight filtering through the trees. In the foreground, two blue chairs are positioned invitingly, and a gas grill is set up nearby, enhancing the outdoor living space.
Cottage in Scarborough
4.97 out of 5 average rating, 211 reviews

Bright, clean, private cottage near Higgins Beach!

OwenRating, 5 stars5 months ago
We loved our stay at the Gull Cottage!! Karen and Steve were great hosts, incredibly friendly, helpful, and responsive. The cottage was well stocked with everything we needed to enjoy our stay. The guide book and guest book were great touches as well, and we would happily stay again next time we come up to Maine! We could not recommend the Gull Cottage more if you’re looking for a great and cozy place to stay near Portland!
Superhost
A recreational room is featured with two pool tables and a large sectional sofa. Various arcade games are visible along the walls, while ample natural light floods through the skylights, creating a welcoming atmosphere for relaxation and entertainment.
Cottage in Wells
4.88 out of 5 average rating, 26 reviews

Best Summer Cottage in Wells Maine. Come and enjoy

JonRating, 5 stars8 months ago
We have been coming to Ogunquit/Wells in the summer for about 10 years, and this was our first time trying Summer Village, and it was a truly fantastic stay! The cottage location is situated between Ogunquit and Wells and is easily accessible to both of those beaches and destinations nearby. ‘A’ could not have been a nicer, more responsive host and it made the logistics of planning very easy. Know going into it that you are bringing your own linens and towels, and there are some standard rules about the larger property, but the cottage has everything you could need and it was very welcoming. In A’s cottage, you have easy ability to sleep a family of 5. There is a fully stocked kitchen and gas grill. But the biggest unexpected perk was all the amenities of the Summer Village property. 3 pools, bocce, tennis, a rec room with games, and a free on-site trolley to get you around every 20 minutes. The stay was incredibly relaxing and I would highly recommend this for young families!
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.
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 stars1 week 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.
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.
Guest favorite
Two red lounge chairs are positioned on the grass overlooking the water. A wooden dock extends into the lake, framed by a potted plant and a large tree to the right. The serene landscape features rolling hills in the distance under a clear blue sky.
Cottage in Alton
4.95 out of 5 average rating, 62 reviews

Lakehurst Lakefront Cottages #3

NancyRating, 5 stars8 months ago
We rented one of the cabins at Lakehurst Cottages for a week in August. We were nervous because we were bringing up our boat and had a bad experience at another lake last year. Jim and Janet were so reassuring as to where we could keep the trailer and the location of a convenient boat launch. It all worked out great! Our cottage was a delightful 1 bedroom with sliders all around. There was everything we needed to cook meals. They have a fire pit with wood if you want to make a fire, or chairs to sit in by the water. Downtown Alton Bay was 4 miles away and we enjoyed walking around during an annual festival and craft fair. The town docks are plentiful and convenient if you have a boat. There is so much to do at Lake Winnipesauke and this cabin was in such a great location with great hosts - and guests!
Superhost
A serene waterfront view is framed by tall trees, offering a glimpse of Songo Pond. An inviting Adirondack chair sits near the water's edge, where a small path leads to a wooden dock. The landscape is lush with vibrant greenery, enhancing the tranquil environment.
Cottage in Bethel
4.89 out of 5 average rating, 28 reviews

Waterfront Cottage- South Shore

CathleenRating, 5 stars22 months ago
We had a great, peaceful and relaxing stay! Everything was as it was pictured. When we had a small issue, Julia and Gary were very responsive and everything was taken care of promptly. The host provided most everything we needed, it made our stay easy to enjoy.

Quick stats about cottage rentals in Windham

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 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

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  2. United States
  3. Maine
  4. Cumberland County
  5. Windham
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