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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Cottages in Windham

Our top choices for Windham cottages

The Purple House by Pettingill Pond
Living area

The Purple House by Pettingill Pond

2.0 star property
9.6 out of 10, Exceptional, (5)
"Beautiful area and clean house, made for a very relaxing weekend"
The Purple House by Pettingill Pond
Luxurious Beachfront New England Cottage
Property grounds

Luxurious Beachfront New England Cottage

10.0 out of 10, Exceptional, (5)
"This house was gorgeous and we highly enjoyed our stay. We will be back!!"
The price is AU$1,452
includes taxes & fees
1 Sept - 2 Sept
Luxurious Beachfront New England Cottage
Charming 2-bedroom Oceanside Cottage in Old Orchard Beach
Beach

Charming 2-bedroom Oceanside Cottage in Old Orchard Beach

10.0 out of 10, Exceptional, (1)
"Just the right size for our family 2 adults 2 kids. Beach is short walk across the street. Cute cottage"
The price is AU$862
includes taxes & fees
22 Sept - 23 Sept
Charming 2-bedroom Oceanside Cottage in Old Orchard Beach
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Exterior detail

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

8.0 out of 10, Very good, (24)
"Property was just as expected. It was nice for us. Only complaint was the grill was broken and we didn’t realize it until after we went and purchased meats for the grill"
The price is AU$377
includes taxes & fees
11 Sept - 12 Sept
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

Cheerful 1 bedroom cottage only 50ft from beach

10.0 out of 10, Exceptional, (2)
"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."
The price is AU$530
includes taxes & fees
14 Sept - 15 Sept
Cheerful 1 bedroom cottage only 50ft from beach
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Beach

The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach

10.0 out of 10, Exceptional, (2)
"Great place for a family retreat "
The price is AU$1,109
includes taxes & fees
11 Sept - 12 Sept
The Rose Cottage, Charming Old Orchard Beach Cottage 25 Steps to Beach
Clean cozy cottage 1 mile from beach.
Fridge, microwave, oven, stovetop

Clean cozy cottage 1 mile from beach.

7.6 out of 10, Good, (9)
"Nice cute cottage."
The price is AU$627
includes taxes & fees
11 Sept - 12 Sept
Clean cozy cottage 1 mile from beach.
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Beach nearby

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

9.4 out of 10, Exceptional, (3)
"Peaceful and close to the beach, had a great stay "
The price is AU$480
includes taxes & fees
3 Sept - 4 Sept
Cozy one bedroom cottage, 50 feet from the beach in OOB.
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, (35)
"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 AU$387
includes taxes & fees
11 Sept - 12 Sept
Large 2BD cottage 10 min to Pier & Beach Pets ok
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Private kitchen

Renovated 2Bd Cottage 10min walk to Beach. Pets Ok

7.2 out of 10, Good, (11)
"Super comfortable beds! Small cozy cottage, but with so much to do in town who needs more space?"
The price is AU$435
includes taxes & fees
1 Sept - 2 Sept
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

Attractive 1 bedroom cabin only 50 ft from beach

The price is AU$515
includes taxes & fees
9 Sept - 10 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Attractive 1 bedroom cabin only 50 ft from beach
Beach nearby

Attractive 1 bedroom cabin only 50 ft from beach

The price is AU$480
includes taxes & fees
1 Sept - 2 Sept
Attractive 1 bedroom cabin only 50 ft from beach
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach nearby

Adorable 1 bedroom cabin only 50 ft from beach#1

The price is AU$480
includes taxes & fees
16 Sept - 17 Sept
Adorable 1 bedroom cabin only 50 ft from beach#1
beautiful 1 bedroom cabin only 50 ft from beach
Exterior detail

beautiful 1 bedroom cabin only 50 ft from beach

The price is AU$495
includes taxes & fees
11 Sept - 12 Sept
beautiful 1 bedroom cabin only 50 ft from beach
Spacious 2 bedroom cabin, 50ft from the beach
Beach nearby

Spacious 2 bedroom cabin, 50ft from the beach

The price is AU$716
includes taxes & fees
11 Sept - 12 Sept
Spacious 2 bedroom cabin, 50ft from the beach
Spring into Summer at Turtle Lane Cottage
Smart TV, fireplace

Spring into Summer at Turtle Lane Cottage

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay while visiting together for a sister's weekend."
The price is AU$481
includes taxes & fees
28 Sept - 29 Sept
Spring into Summer at Turtle Lane Cottage
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.
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Top Windham Hotel Reviews

Find out more about Windham

Find out more about Windham

Windham Cottages information

Number of reviews
353
Accommodation
458 Cottages
Lowest Price
AU$387
Highest Price
AU$387

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Windham cost?
Prices for cottages in Windham range between AU$387 and AU$387 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 458 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.