Cottage holiday rentals in Windham
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Top-rated cottage rentals in Windham
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham cottage rentals
Cottage rentals with a hot tub
Cottage in Middleton
4.96 out of 5 average rating, 139 reviews☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
30 Aug – 6 Sept
Cottage in Conway
4.89 out of 5 average rating, 295 reviewsHOT TUB! Amazing view. Hike, Bike, Swim!
31 July – 7 Aug
Cottage in Norway
4.96 out of 5 average rating, 117 reviewsCottage with Whirlpool tub - Ross
26 Aug – 2 Sept
Cottage in York
4.98 out of 5 average rating, 146 reviewsAdorable cottage by Shorts Sands Beach
17 – 24 Sept
Cottage in Wells
4.93 out of 5 average rating, 135 reviewsCozy Cottage with Ocean Views, Wells Maine
11 – 18 Sept
Cottage in Wells
4.97 out of 5 average rating, 38 reviews2 BR house, close to Ogunquit, w/ AC + golf cart!
1 – 8 Oct
Cottage in Wells
4.98 out of 5 average rating, 47 reviewsFreshly Renovated, Family-Friendly Coastal Cottage
16 – 23 Sept
Cottage in Northwood
4.96 out of 5 average rating, 68 reviewsThe Loon Nest, Waterfront Lake House, Wood Hot Tub
24 – 31 Oct
Pet-friendly cottage rentals
Cottage in Northwood
4.91 out of 5 average rating, 214 reviewsCottage near lake! Includes canoe! Dog friendly!
15 – 22 Sept
Cottage in Old Orchard Beach
4.98 out of 5 average rating, 172 reviews#3 Couples Cottage Minutes from the Beach
7 – 14 Nov
Cottage in Freedom
4.78 out of 5 average rating, 441 reviewsLakefront, Beach Private, Amazing Views, & pets!
11 – 18 Dec
Cottage in Wiscasset
4.87 out of 5 average rating, 211 reviewsWaterscape Cottage - private waterfront
17 – 24 Nov
Cottage in Brownfield
4.86 out of 5 average rating, 127 reviewsTompeca Cottage - Pet Friendly
3 – 10 Sept
Cottage in Wakefield
4.93 out of 5 average rating, 144 reviewsLake View Cottage / Fenced in Yard
18 – 25 Nov
Cottage in Alton
4.87 out of 5 average rating, 159 reviews1 Bedroom Cottage w/Lake Winnipesaukee View/Access
22 – 29 Oct
Cottage in Phippsburg
4.85 out of 5 average rating, 158 reviewsPopham - Tidewater Beach House!
26 Sept – 3 Oct
Private cottage rentals
Cottage in Conway
4.95 out of 5 average rating, 281 reviews20ft from the Water with Mountain View!
12 – 19 Dec
Cottage in Sabattus
4.96 out of 5 average rating, 102 reviewsMaine lakehouse- close to Portland, 2.5 hr. Boston
15 – 22 Dec
Cottage in Jackson
4.98 out of 5 average rating, 291 reviewsThe River House In Jackson NH, R&M # 059525
23 – 30 Apr
Cottage in Bath
4.88 out of 5 average rating, 499 reviewsDoubling Point Cottage
23 – 28 July
Cottage in Harpswell
4.9 out of 5 average rating, 124 reviewsClassic Maine Cottage - dock, sauna & kayaks
3 – 10 Oct
Cottage in Windham
4.89 out of 5 average rating, 62 reviewsCovered Bridge Cottage - Maine woods and river
8 – 15 Nov
Cottage in Windham
5.0 out of 5 average rating, 65 reviewsRomantic waterfront cottage for two in Maine
9 – 16 May
Cottage in Windham
4.9 out of 5 average rating, 10 reviewsRelaxing 2 bed cottage on Little Sebago Lake
11 – 18 May
Quick stats about cottage rentals in Windham
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$138 AUD before taxes and fees
Destinations to explore
- Portland Holiday rentals
- Salem Holiday rentals
- Chebacco Lake Accommodation & holiday rentals
- Old Orchard Beach Holiday rentals
- Lake Winnipesaukee Accommodation & holiday rentals
- Jersey City Holiday rentals
- New York Accommodation & holiday rentals
- The Hamptons Holiday rentals
- Boston Accommodation & holiday rentals
- Montreal Accommodation & holiday rentals
- Québec City Accommodation & holiday rentals
- Québec Accommodation & holiday rentals
- Cottage rentals Maine
- Cottage rentals New Hampshire
- Cottage rentals Portland
- Rentals with beach access Windham
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- Monthly Rentals Windham
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- Rentals with lake access Windham
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- Rentals with a washing machine and dryer Windham
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