Windham Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Windham vacation rentals

Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is ￥26,485
￥46,555 total
includes taxes & fees
May 21 - May 22
Modern, Luxurious Cabin in the Woods - 03
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is ￥30,064
￥52,883 total
includes taxes & fees
May 21 - May 22
Large, luxurious geodesic dome - 04
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is ￥19,876
￥39,004 total
includes taxes & fees
May 21 - May 22
Peaceful & minutes from the Old Port with private parking
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is ￥48,375
￥92,673 total
includes taxes & fees
May 26 - May 27
Mere Point Sunrise Views at Eastern Shore!
Smart TV, fireplace

Sunny Cottage

Sunny Cottage
Biddeford
10.0 out of 10, Exceptional, (51 reviews)
"The property is in a great location. It was very clean and the beds were comfortable! "
United States
Jamie B.
The price is ￥20,902
￥43,590 total
includes taxes & fees
May 27 - May 28
Sunny Cottage
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is ￥19,335
￥36,507 total
includes taxes & fees
May 21 - May 22
Sunny Spot with Private Parking.
Interior

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, (69 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is ￥24,195
￥45,098 total
includes taxes & fees
May 27 - May 28
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is ￥25,769
￥48,028 total
includes taxes & fees
May 31 - Jun 1
Pine Point Beach private, quaint, charming studio.
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ￥32,212
￥58,692 total
includes taxes & fees
May 27 - May 28
Full sized home
Beach nearby, sun loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (38 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is ￥20,100
￥54,332 total
includes taxes & fees
May 27 - May 28
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Outdoor dining

THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (9 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
The price is ￥23,030
￥28,565 total
includes taxes & fees
Jun 13 - Jun 14
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Property grounds

Welcome to our BoHo Treehouse!

Welcome to our BoHo Treehouse!
Downtown Saco
9.8 out of 10, Exceptional, (9 reviews)
"Walkable to restaurants and shops and very easy process! "
United States
Meg B.
The price is ￥20,679
￥43,346 total
includes taxes & fees
May 21 - May 22
Welcome to our BoHo Treehouse!
Dining

The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly

The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly
Downtown Saco
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful home, well appointed, clean and updated, great space! Would definitely stay again. "
United States
Lucy T.
The price is ￥23,216
￥58,596 total
includes taxes & fees
May 27 - May 28
The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly
Exterior

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (10 reviews)
"Very private property, was a great little retreat. Such a thoughtfully designed space, and loved being surrounded by nature, including breakfast with deer!"
United States
Dan M.
The price is ￥55,675
￥99,004 total
includes taxes & fees
May 25 - May 26
Cozy Rock Cabin #thewaylifeshouldbe
Interior

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco
Saco
9.6 out of 10, Exceptional, (5 reviews)
"The coastal condo was comfortable and a great place to stay! "
United States
Tara P.
The price is ￥17,895
￥51,063 total
includes taxes & fees
May 25 - May 26
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco
Exterior

A historic treasure in Southern Maine, very unique and spacious

A historic treasure in Southern Maine, very unique and spacious
Biddeford
10.0 out of 10, Exceptional, (44 reviews)
"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "
United States
Jeanne C.
The price is ￥81,889
￥160,347 total
includes taxes & fees
May 21 - May 22
A historic treasure in Southern Maine, very unique and spacious
Property grounds

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (10 reviews)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is ￥33,810
￥74,813 total
includes taxes & fees
May 21 - May 22
Orchid Harbor, Bailey Island 3BR
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is ￥60,216
￥65,635 total
includes taxes & fees
Jun 7 - Jun 8
Fortland Island Campground
1 bedroom, internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is ￥27,837
￥44,040 total
includes taxes & fees
May 21 - May 22
Charming 1-bedroom ADU in wonderful Portland neighborhood
Interior

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Saco
9.2 out of 10, Wonderful, (15 reviews)
"Had a great stay, very private property. House was very clean and user friendly. Would definitely stay again, thanks"
United States
Doug C.
The price is ￥42,949
￥52,883 total
includes taxes & fees
May 26 - May 27
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
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

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent
"Breakfast was just bagels and cereal. Staff didn’t come to do the beds after it said they’d come every other day. Good quality."
Annaliz 4-night trip
Posted 2 hours ago
Spark by Hilton Portland Airport Maine Mall

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
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  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

Look no further and take a look at our great range of rental properties in Windham!

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Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Seacoast Adventure, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

The Lookout by Bayley Vacation Rentals: This vacation home rental near Windham is located by the ocean and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Windham?

Expedia has 34 vacation rentals for your stay in Windham.

What can I see and do in Windham?

Sebago Lake Basin and Little Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake and Jordan Bay.

What are vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.