Search Windham Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Windham cottages

A two-story building with a metal exterior, a door with a cactus and a cow design, and three windows with decorative panels.

1. Cozy 1-bedroom cottage in soothing Standish with AC

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
10.0 out of 10, Exceptional, (4 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
The price is AU$424
includes taxes & fees
29 Nov - 30 Nov
Cozy 1-bedroom cottage in soothing Standish with AC
A two-story house with a front porch, a garage, and a well-maintained lawn.

2. Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (100 reviews)
"Pet friendly, clean cottage in quiet neighborhood."
United States
Alejandra
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
A two-story house with a gabled roof and a front porch.

3. 3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"Super clean and spacious in a walkable area. "
United States
Nell F.
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
A two-story house with a white exterior and a black base. There is a white staircase leading to the front door, surrounded by lush greenery and flowering plants.

4. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (22 reviews)
"Great house! Wonderful location with so many wonderful touches to make our stay so comfortable. We would definitely stay there again."
United States
Anonymous traveller
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A pier with a building on stilts over the beach.

5. beautiful 1 bedroom cabin only 50 ft from beach

beautiful 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Being so close to the water was great. Place was a little smaller than we typically get but sufficient and was very clean. The owner was great to communicate with and quick to respond to questions. We particularly liked the shaded patio area in front."
United States
Allan S.
The price is AU$374
includes taxes & fees
6 Dec - 7 Dec
beautiful 1 bedroom cabin only 50 ft from beach
An aerial view of a coastal resort with multiple buildings, a swimming pool, and a beach.

6. Little Miss Cottages 1-4: 1BR by Everrow

Little Miss Cottages 1-4: 1BR by Everrow
Old Orchard Beach
9.4 out of 10, Exceptional, (26 reviews)
"Loved the proximity to the beach and general store. The host was very responsive, the bed was comfortable, cottage was clean and we had plenty of hot water for showers. My husband and I had a great stay and would consider booking again in the future!"
United States
Mallory P.
The price is AU$490
includes taxes & fees
15 Nov - 16 Nov
Little Miss Cottages 1-4: 1BR by Everrow
A lakeside house with a dock, a small boathouse, and a flag.

7. Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
Brownfield
10.0 out of 10, Exceptional, (6 reviews)
"Great little camp with lake access! Thanks for hosting us :-)"
United States
Anonymous traveller
The price is AU$498
includes taxes & fees
1 Dec - 2 Dec
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
A beach with people, a pier, and an American flag.

8. Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach

Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
Old Orchard Beach
8.2 out of 10, Very good, (28 reviews)
"Even though the property was small it was spacious for two people especially my husband and I we had an awesome awesome week there the host was unbelievably kind the woman Kathy that clean the unit was exceptional and very very nice the neighborhood was peaceful and it was very convenient to the pier and all the shops definitely will be staying there from now on every year it was awesome"
United States
Catherine
The price is AU$485
includes taxes & fees
15 Nov - 16 Nov
Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
A pier extending into calm waters with a building at the end.

9. Cozy one bedroom cottage, 50 feet from the beach in OOB.

Cozy one bedroom cottage, 50 feet from the beach in OOB.
Old Orchard Beach
9.8 out of 10, Exceptional, (6 reviews)
"Nice place"
United States
Brad G.
The price is AU$374
includes taxes & fees
8 Dec - 9 Dec
Cozy one bedroom cottage, 50 feet from the beach in OOB.
A two-story house with a front porch, a bench, and a well-maintained lawn.

10. Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (11 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is AU$369
includes taxes & fees
19 Nov - 20 Nov
Adorable 1 bedroom cabin only 50 ft from beach#1
A rustic building with a pond, stone pathway, and flower beds.

11. Cheerful 1 bedroom cottage only 50ft from beach

Cheerful 1 bedroom cottage only 50ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (5 reviews)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
The price is AU$376
includes taxes & fees
15 Dec - 16 Dec
Cheerful 1 bedroom cottage only 50ft from beach
A beach with waves gently lapping at the shore.

12. Attractive 1 bedroom cabin only 50 ft from beach

Attractive 1 bedroom cabin only 50 ft from beach
Old Orchard Beach
9.6 out of 10, Exceptional, (5 reviews)
"Great place! Loved being on the end so we only had one neighbor. No crazy list of things to do at check out was much appreciated."
United States
Mandy H.
The price is AU$357
includes taxes & fees
24 Nov - 25 Nov
Attractive 1 bedroom cabin only 50 ft from beach
A house with a number '2' on the side, a door, and a window.

13. Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach

Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Super comfortable beds! Small cozy cottage, but with so much to do in town who needs more space?"
United States
John G.
The price is AU$473
includes taxes & fees
15 Nov - 16 Nov
Sleeps 5 • 2BR • OOB • 10-min walk to Pier & Beach
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.
View all properties

Learn more about Windham

Outdoor enthusiasts flock to Dundee Park's sandy beach for swimming and picnicking on Pleasant River's shores. Windham's historic district reveals 19th-century charm, while nearby Sebago Lake State Park offers prime fishing and boating.

See all hotels in Windham
A white church with a steeple and red accents, surrounded by autumn trees.

Top reviews in Windham

A multi-story hotel with a covered entrance and a parking area.
Dormir

Dormir

Dormir
Windham

10/10 Excellent

One of the only nice places to stay near Sebago. Reasonable prices and super nice employees with good suggestions for food and hiking. Highly recommend compared to other local options. Clean and new accomodations.
Australia
James
Reviewed October 5, 2019
Dormir

Frequently Asked Questions

How much do cottages in Windham cost?

Prices for cottages in Windham range between AU$356 and AU$497 per night. Whatever your budget, you're sure to find a perfect place to get reacquainted with nature. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Windham?

Surround yourself with nature in one of the cottages waiting for you in Windham. To help you find your ideal place, use our handy filter tool to search for perks or amenities you need.

What is there to do in Windham near my cottage?

Windham has enough sights and activities to keep you going for weeks, beginning with Seacoast Adventure. Maine Wildlife Park, Childrens Museum and Theatre of Maine and Southworth Planetarium are other wonderful attractions. If you're sticking around a while, Thompsons Point and University of Southern Maine are nice final touches to your itinerary.