Cottage vacation 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.
Vacation 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 Conway
4.89 out of 5 average rating, 295 reviewsHOT TUB! Amazing view. Hike, Bike, Swim!
Nov 30 – Dec 7
Cottage in Norway
4.96 out of 5 average rating, 118 reviewsCottage with Whirlpool tub - Ross
Dec 1 – 8
Cottage in York
4.98 out of 5 average rating, 146 reviewsAdorable cottage by Shorts Sands Beach
Feb 19 – 26
Cottage in Wells
4.93 out of 5 average rating, 135 reviewsCozy Cottage with Ocean Views, Wells Maine
Sep 8 – 15
Cottage in Wells
4.98 out of 5 average rating, 47 reviewsFreshly Renovated, Family-Friendly Coastal Cottage
Sep 23 – 30
Cottage in Gilmanton
4.9 out of 5 average rating, 10 reviewsCozy Cottage on a Lake, near Gunstock Mountain
Nov 2 – 9
Cottage in Wells
4.97 out of 5 average rating, 38 reviews2 BR house, close to Ogunquit, w/ AC + golf cart!
Oct 1 – 8
Cottage in Gilmanton
4.85 out of 5 average rating, 59 reviewsCamp with hot tub, Gunstock, lake & fire pit!
Sep 27 – Oct 4
Pet-friendly cottage rentals
Cottage in Saco
4.93 out of 5 average rating, 313 reviewsDeja Blue~Guest Beach House
Nov 26 – Dec 3
Cottage in Parsonsfield
4.9 out of 5 average rating, 120 reviewsRiverpine Retreat - clean&bright waterfront home
Jun 8 – 15
Cottage in Old Orchard Beach
4.98 out of 5 average rating, 173 reviews#3 Couples Cottage Minutes from the Beach
Feb 11 – 18
Cottage in Northwood
4.91 out of 5 average rating, 214 reviewsCottage near lake! Includes canoe! Dog friendly!
Dec 11 – 18
Cottage in Wiscasset
4.87 out of 5 average rating, 211 reviewsWaterscape Cottage - private waterfront
Nov 26 – Dec 3
Cottage in Brownfield
4.86 out of 5 average rating, 127 reviewsTompeca Cottage - Pet Friendly
Apr 8 – 15
Cottage in Freedom
4.78 out of 5 average rating, 441 reviewsLakefront, Beach Private, Amazing Views, & pets!
Dec 20 – 27
Cottage in Wakefield
4.93 out of 5 average rating, 144 reviewsLake View Cottage / Fenced in Yard
Nov 29 – Dec 6
Private cottage rentals
Cottage in Middleton
4.96 out of 5 average rating, 136 reviewsBeautiful Lakeside Cottage
Sep 27 – Oct 4
Cottage in Harpswell
4.9 out of 5 average rating, 124 reviewsClassic Maine Cottage - dock, sauna & kayaks
Oct 3 – 10
Cottage in Conway
4.95 out of 5 average rating, 282 reviews20ft from the Water with Mountain View!
Dec 11 – 18
Cottage in Sabattus
4.96 out of 5 average rating, 103 reviewsMaine lakehouse- close to Portland, 2.5 hr. Boston
Dec 15 – 22
Cottage in Livermore
4.95 out of 5 average rating, 140 reviewsBass Point Lakeside Cottage: Livermore, Maine
Feb 3 – 10
Cottage in Bath
4.88 out of 5 average rating, 499 reviewsDoubling Point Cottage
Jul 23 – 28
Cottage in Epsom
4.97 out of 5 average rating, 189 reviewsSmokey Pines Camp
Sep 26 – Oct 3
Cottage in Windham
5.0 out of 5 average rating, 65 reviewsRomantic waterfront cottage for two in Maine
May 10 – 17
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
€ 84 before taxes and fees
Destinations to explore
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