
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

Cozy Cottage close to Beach, Pool and more!
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

Charming Quiet Cottage close to hiking & JXN Falls
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!

Cozy beach cottage with pool & hot tub
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!

Lakeside Cozy Cottage in Nature | Hot Tub
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!

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

Beautifully renovated 2-bedroom cottage
Everything was so perfect !! thank you for hosting us !!

Contemporary Cottage With Ocean View 13
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.

Vintage Maine 2 Bedroom Cottage
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

Lovely cottage on Sunrise Lake, Middleton, NH.
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.

Cottage on Todd Bay
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.

Osprey Cottage, peaceful setting, walk to beach
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.

Pet Friendly Audubon Bring Your Fishing Gear!
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!

Sunset Haven - Little Sebago Lake
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!

Rustic Pebble Cottage in beautiful Bridgton, Maine
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!

Cozy Cottage on Highland Lake
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!

H and K Cove View Cottage LLC
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

Cheerful 1 Bedroom Cottage Steps From The Ocean
Wonderful place clean and very cozy house I indicate

Bright, clean, private cottage near Higgins Beach!
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!

Best Summer Cottage in Wells Maine. Come and enjoy
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!

Lake view cottage #1 in Alton Bay on Winnipesaukee
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.

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom
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.

Seaside Escape
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.

Lakehurst Lakefront Cottages #3
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!

Waterfront Cottage- South Shore
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
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- Wells Beach
- Attitash Mountain Resort
- Story Land
- Cranmore Mountain Resort
- Ogunquit Playhouse
- East End Beach
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- Mt. Abram
- King Pine Ski Area
- Bald Peak Colony Club
- Diana's Baths
- Parsons Beach
- Portland Museum of Art
- Mothers Beach
- Ferry Beach
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Jackson Xc