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
Oct 29 – Nov 5
Cottage in Conway
4.9 out of 5 average rating, 296 reviewsHOT TUB! Amazing view. Hike, Bike, Swim!
Oct 26 – Nov 2
Cottage in Norway
4.96 out of 5 average rating, 118 reviewsCottage with Whirlpool tub - Ross
Jul 10 – 17
Cottage in York
4.98 out of 5 average rating, 146 reviewsAdorable cottage by Shorts Sands Beach
Oct 21 – 28
Cottage in Wells
4.93 out of 5 average rating, 135 reviewsCozy Cottage with Ocean Views, Wells Maine
Nov 17 – 24
Cottage in Wells
4.98 out of 5 average rating, 47 reviewsFreshly Renovated, Family-Friendly Coastal Cottage
Sep 23 – 30
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 Northwood
4.96 out of 5 average rating, 69 reviewsThe Loon Nest, Waterfront Lake House, Wood Hot Tub
Sep 10 – 17
Pet-friendly cottage rentals
Cottage in Old Orchard Beach
4.98 out of 5 average rating, 174 reviews#3 Couples Cottage Minutes from the Beach
Dec 30 – Jan 6
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!
Feb 24 – Mar 3
Cottage in Freedom
4.79 out of 5 average rating, 442 reviewsLakefront, Beach Private, Amazing Views, & pets!
Mar 19 – 26
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
Jan 13 – 20
Cottage in Wakefield
4.93 out of 5 average rating, 144 reviewsLake View Cottage / Fenced in Yard
Nov 2 – 9
Cottage in Alton
4.87 out of 5 average rating, 159 reviews1B Cottage w/kayaks-Lake Winnipesaukee View/Access
Sep 19 – 26
Private cottage rentals
Cottage in Bath
4.88 out of 5 average rating, 499 reviewsDoubling Point Cottage
Jul 23 – 28
Cottage in Conway
4.95 out of 5 average rating, 282 reviews20ft from the Water with Mountain View!
Nov 3 – 10
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 Harpswell
4.9 out of 5 average rating, 124 reviewsClassic Maine Cottage - dock, sauna & kayaks
Oct 3 – 10
Cottage in Livermore
4.95 out of 5 average rating, 140 reviewsBass Point Lakeside Cottage: Livermore, Maine
Nov 26 – Dec 3
Cottage in Jackson
4.98 out of 5 average rating, 291 reviewsThe River House In Jackson NH, R&M # 059525
Nov 1 – 8
Cottage in Windham
5.0 out of 5 average rating, 65 reviewsRomantic waterfront cottage for two in Maine
May 10 – 17
Cottage in Windham
4.89 out of 5 average rating, 63 reviewsCovered Bridge Cottage - Maine woods and river
Nov 11 – 18
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
$90 before taxes and fees
Destinations to explore
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