A white church with a steeple and red accents, surrounded by autumn trees.

Windham Vacation Rentals

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Our top choices for Windham vacation rentals

Cozy 1 BR ADU | Private Access | Projector Theater

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very clean! Small space (no microwave) pet friendly and very accommodating to our travel needs!"
United States
Traci P.
The price is CA $217
CA $693 total
includes taxes & fees
Jul 18 - Jul 19
Cozy 1 BR ADU | Private Access | Projector Theater

Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is CA $372
CA $1,151 total
includes taxes & fees
Jul 24 - Jul 25
Windham Lakefront: Fire Pit and Modern Comforts

Sebago Basin Retreat | Sleeps 12 | Beach Access | Mooring | Kayaks | Fire Pit

Sebago Basin Retreat | Sleeps 12 | Beach Access | Mooring | Kayaks | Fire Pit
Windham
The price is CA $1,026
CA $1,814 total
includes taxes & fees
Jul 14 - Jul 15
Sebago Basin Retreat | Sleeps 12 | Beach Access | Mooring | Kayaks | Fire Pit

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 $482
CA $526 total
includes taxes & fees
Jul 12 - Jul 13
Fortland Island Campground

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (12 reviews)
"Had so much fun! Our dog had a blast, and we got the cozy reset we needed "
United States
Maureen L.
The price is CA $974
CA $1,477 total
includes taxes & fees
Jul 14 - Jul 15
Cozy Rock Cabin #thewaylifeshouldbe

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is CA $173
CA $415 total
includes taxes & fees
Jul 16 - Jul 17
1 Mi to Maine Street! Mcm-style Home in Brunswick

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, (78 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is CA $350
CA $569 total
includes taxes & fees
Jul 15 - Jul 16
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (28 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 $294
CA $476 total
includes taxes & fees
Jul 12 - Jul 13
Sunny Spot with Private Parking.

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (35 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is CA $297
CA $512 total
includes taxes & fees
Aug 9 - Aug 10
Pine Point Beach private, quaint, charming studio.

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (47 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
The price is CA $212
CA $477 total
includes taxes & fees
Aug 10 - Aug 11
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $318
CA $565 total
includes taxes & fees
Jul 29 - Jul 30
Full sized home

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)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is CA $334
CA $544 total
includes taxes & fees
Jul 12 - Jul 13
Peaceful & minutes from the Old Port with private parking

'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is CA $466
CA $916 total
includes taxes & fees
Jul 19 - Jul 20
'Osprey Cottage' South Freeport Home on Casco Bay!

Secluded A-Frame Cabin Retreat in Oxford

Secluded A-Frame Cabin Retreat in Oxford
Oxford
10.0 out of 10, Exceptional, (2 reviews)
"Peaceful, beautiful, and everything we wanted ( exception of rain)! Would highly recommend and ca not wait to go back!"
United States
Kelly S.
The price is CA $317
CA $568 total
includes taxes & fees
Jul 12 - Jul 13
Secluded A-Frame Cabin Retreat in Oxford

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, (44 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveller
The price is CA $206
CA $517 total
includes taxes & fees
Jul 19 - Jul 20
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Sunny Cottage

Sunny Cottage
Biddeford
10.0 out of 10, Exceptional, (54 reviews)
"Exactly as described, close to everything."
United States
Erika J.
The price is CA $268
CA $491 total
includes taxes & fees
Jul 12 - Jul 13
Sunny Cottage

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, (10 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
The price is CA $331
CA $412 total
includes taxes & fees
Jul 12 - Jul 13
THE LILLIPAD.Off-grid A frame. Sebago lake region!

New Listing! AmongstTheAspens - Off-Grid Tiny Home

New Listing! AmongstTheAspens - Off-Grid Tiny Home
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 $394
CA $490 total
includes taxes & fees
Jul 12 - Jul 13
New Listing! AmongstTheAspens - Off-Grid Tiny Home

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Downtown Saco
10.0 out of 10, Exceptional, (25 reviews)
"Great space, responsive host, great location!"
United States
Reed C.
The price is CA $251
CA $533 total
includes taxes & fees
Jul 15 - Jul 16
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is CA $313
CA $561 total
includes taxes & fees
Jul 12 - Jul 13
The Barnhouse with hot tub
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?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private Bathroom “No Kitchen”: This vacation home rental near Windham is located on the beach and offers a fireplace, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and an electric kettle.

How many vacation rentals are there in Windham?

Expedia has 35 vacation rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and 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 Basin and Forest Lake.

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.