Windham Vacation Rentals

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Our top choices for Windham vacation rentals

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 CA $250
CA $434 total
includes taxes & fees
May 21 - May 22
Modern, Luxurious Cabin in the Woods - 03

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 CA $284
CA $494 total
includes taxes & fees
May 21 - May 22
Large, luxurious geodesic dome - 04

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 CA $172
CA $340 total
includes taxes & fees
May 21 - May 22
Peaceful & minutes from the Old Port with private parking

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 CA $418
CA $800 total
includes taxes & fees
May 26 - May 27
Mere Point Sunrise Views at Eastern Shore!

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 CA $181
CA $379 total
includes taxes & fees
May 27 - May 28
Sunny Cottage

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 CA $167
CA $317 total
includes taxes & fees
May 21 - May 22
Sunny Spot with Private Parking.

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 CA $204
CA $383 total
includes taxes & fees
May 26 - May 27
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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 CA $223
CA $415 total
includes taxes & fees
May 31 - Jun 1
Pine Point Beach private, quaint, charming studio.

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $278
CA $504 total
includes taxes & fees
May 27 - May 28
Full sized home

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 CA $175
CA $474 total
includes taxes & fees
May 27 - May 28
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

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 CA $199
CA $247 total
includes taxes & fees
Jun 12 - Jun 13
THE LILLIPAD.Off-grid A frame. Sebago lake region!

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 CA $179
CA $394 total
includes taxes & fees
May 31 - Jun 1
Welcome to our BoHo Treehouse!

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 CA $211
CA $520 total
includes taxes & fees
May 26 - May 27
The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly

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 CA $481
CA $855 total
includes taxes & fees
May 31 - Jun 1
Cozy Rock Cabin #thewaylifeshouldbe

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 CA $155
CA $441 total
includes taxes & fees
May 26 - May 27
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

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 CA $707
CA $1,385 total
includes taxes & fees
May 21 - May 22
A historic treasure in Southern Maine, very unique and spacious

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 CA $262
CA $618 total
includes taxes & fees
May 21 - May 22
Orchid Harbor, Bailey Island 3BR

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 CA $520
CA $567 total
includes taxes & fees
Jun 4 - Jun 5
Fortland Island Campground

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is CA $240
CA $383 total
includes taxes & fees
May 21 - May 22
Charming 1-bedroom ADU in wonderful Portland neighborhood

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 CA $371
CA $461 total
includes taxes & fees
May 27 - May 28
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

Find out more about Windham

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.