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 Middleton
4.96 out of 5 average rating, 141 reviews☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
Aug 30 – Sep 6
Cottage in Conway
4.9 out of 5 average rating, 296 reviewsHOT TUB! Amazing view. Hike, Bike, Swim!
Jun 11 – 18
Cottage in Norway
4.96 out of 5 average rating, 118 reviewsCottage with Whirlpool tub - Ross
Jul 11 – 18
Cottage in York
4.98 out of 5 average rating, 146 reviewsAdorable cottage by Shorts Sands Beach
Oct 20 – 27
Cottage in Wells
4.93 out of 5 average rating, 135 reviewsCozy Cottage with Ocean Views, Wells Maine
Dec 27 – Jan 3
Cottage in Gilmanton
4.91 out of 5 average rating, 11 reviewsCozy Cottage on a Lake, near Gunstock Mountain
Oct 8 – 15
Cottage in Gilmanton
4.85 out of 5 average rating, 59 reviewsCamp with hot tub, Gunstock, lake & fire pit!
Sep 16 – 23
Cottage in Wells
4.98 out of 5 average rating, 47 reviewsFreshly Renovated, Family-Friendly Coastal Cottage
Sep 17 – 24
Pet-friendly cottage rentals
Cottage in Kittery
4.95 out of 5 average rating, 139 reviewsCozy Maine Cottage by the Sea
Oct 27 – Nov 3
Cottage in Parsonsfield
4.9 out of 5 average rating, 120 reviewsRiverpine Retreat - clean&bright waterfront home
Jun 8 – 15
Cottage in Northwood
4.91 out of 5 average rating, 216 reviewsCottage near lake! Includes canoe! Dog friendly!
Dec 22 – 29
Cottage in Old Orchard Beach
4.98 out of 5 average rating, 174 reviews#3 Couples Cottage Minutes from the Beach
Nov 2 – 9
Cottage in Freedom
4.79 out of 5 average rating, 442 reviewsLakefront, Beach Private, Amazing Views, & pets!
Mar 19 – 26
Cottage in Alton
4.87 out of 5 average rating, 159 reviews1B Cottage w/kayaks-Lake Winnipesaukee View/Access
Nov 29 – Dec 6
Cottage in Brownfield
4.86 out of 5 average rating, 127 reviewsTompeca Cottage - Pet Friendly
Apr 10 – 17
Cottage in Wiscasset
4.87 out of 5 average rating, 211 reviewsWaterscape Cottage - private waterfront
Nov 4 – 11
Private cottage rentals
Cottage in Bath
4.88 out of 5 average rating, 499 reviewsDoubling Point Cottage
Jul 23 – 28
Cottage in Livermore
4.95 out of 5 average rating, 140 reviewsBass Point Lakeside Cottage: Livermore, Maine
Feb 9 – 16
Cottage in Conway
4.95 out of 5 average rating, 282 reviews20ft from the Water with Mountain View!
Mar 20 – 27
Cottage in Harpswell
4.9 out of 5 average rating, 125 reviewsClassic Maine Cottage - dock, sauna & kayaks
Oct 3 – 10
Cottage in Windham
5.0 out of 5 average rating, 65 reviewsRomantic waterfront cottage for two in Maine
May 10 – 17
Cottage in Windham
4.85 out of 5 average rating, 48 reviewsThe Purple House by Pettingill Pond
May 8 – 15
Cottage in Windham
4.89 out of 5 average rating, 63 reviewsCovered Bridge Cottage - Maine woods and river
Oct 10 – 17
Cottage in Windham
4.9 out of 5 average rating, 10 reviewsRelaxing 2 bed cottage on Little Sebago Lake
Sep 24 – Oct 1
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
ﺩ.ﺇ331 before taxes and fees
Destinations to explore
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