Search Windham Cottage Rentals from CA $241

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windham Cottages

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Exterior

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (39)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Property grounds

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

9.6 out of 10, Exceptional, (49)
"We had a wonderful time at this house! It’s perfectly situated by the beach, just a stone’s throw away from the charming village of Biddeford Pool. You can even grab some fresh, steamed lobster at the grocery store there. The house offers breathtaking views of the sunset and the bay, and there’s plenty of great outdoor space for relaxation. Parking is also a breeze. The host is incredibly friendly and responsive, making our stay even more enjoyable. We even had a travel massage for our...
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Exterior

Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

9.6 out of 10, Exceptional, (4)
"This was a gem, and the location was perfect for what we need. Very charming and such a comfortable bed"
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
WATERFRONT ON PETTENGILL POND
Exterior

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
Little Miss Cottages
Exterior

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (86)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
Exterior

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

10.0 out of 10, Exceptional, (9)
"Good location, good fishing"
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (2)
"Cute cabin in small quiet campground close to pool and short walk to downtown. The cabin itself was clean, cozy, and had everything we needed for a comfortable stay. Perfect for a small family getaway or a relaxing weekend."
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
The Great Escape - Picturesque Sebago Lake
Terrace/patio

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (50)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (33)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is CA $241
CA $425 total
includes taxes & fees
Sep 1 - Sep 2
Large 2BD cottage 10 min to Pier & Beach Pets ok
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Exterior

Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!

9.6 out of 10, Exceptional, (45)
"We enjoyed our visit"
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Exterior

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

9.8 out of 10, Exceptional, (119)
"I stayed at the end of April, so it was very quiet. The location is great right on the river. The cabin is cozy. Host was very responsive and friendly."
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
3 BR Lake house in Sebago Maine steps from beach!
Exterior

3 BR Lake house in Sebago Maine steps from beach!

10.0 out of 10, Exceptional, (1)
"Close to the beach boat rentals and restaurants. Far enough away from the noise. Clean house with all the amenities needed. Philip was great and always available."
3 BR Lake house in Sebago Maine steps from beach!
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Quaint Cottage Just Steps From The Beach And The Saco River
Exterior

Quaint Cottage Just Steps From The Beach And The Saco River

9.8 out of 10, Exceptional, (16)
"We had a very nice, clean and comfortable stay!"
Quaint Cottage Just Steps From The Beach And The Saco River
Dock + Fire Pit: Secluded Cottage in Denmark
Outdoor dining

Dock + Fire Pit: Secluded Cottage in Denmark

8.0 out of 10, Very good, (1)
"The lake is beautiful and all of the kayaks and other water gear to enjoy it was much appreciated! The only thing that wasn't clearly explained in the description is that the master bedroom is its own separate structure (so you have to go outside the main cabin to get to it). This was not a problem for us because our kids are older, but if you have very small kiddos, this is important to know. But the cabin has just about everything you could possibly need, all stored very artfully in the...
Dock + Fire Pit: Secluded Cottage in Denmark
Waterfront Lake Arrowhead Home w/ Kayaks & Grill!
Property grounds

Waterfront Lake Arrowhead Home w/ Kayaks & Grill!

9.4 out of 10, Exceptional, (22)
"We enjoyed our stay. It was comfy cozy."
Waterfront Lake Arrowhead Home w/ Kayaks & Grill!
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Outdoor dining

'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!

10.0 out of 10, Exceptional, (12)
"Really enjoyed the house and location."
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

10/10 Excellent
"I enjoyed my stay and thought was excellent value for the money. For old property it has been kept up well. I enjoyed they had pool and strong AC in the rooms. "
Elizabeth 1-night trip
Posted 1 day ago
Days Inn by Wyndham Airport/Maine Mall