Windham Vacation Rentals

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Our top choices for Windham vacation rentals

Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake
Windham
10.0 out of 10, Exceptional, (4 reviews)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is CA $185
CA $231 total
includes taxes & fees
Feb 10 - Feb 11
Spacious Studio Near Sebago Lake

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
Windham
The price is CA $223
CA $942 total
includes taxes & fees
Feb 10 - Feb 11
Modern Lakeview Escape | 3BR/2BA

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (9 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 $376
CA $721 total
includes taxes & fees
Feb 19 - Feb 20
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 $100
CA $314 total
includes taxes & fees
Feb 24 - Feb 25
1 Mi to Maine Street! Mcm-style Home in Brunswick

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (26 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 $120
CA $286 total
includes taxes & fees
Feb 10 - Feb 11
Pine Point Beach private, quaint, charming studio.

Modern, luxurious cabin in the woods - 21

Modern, luxurious cabin in the woods - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is CA $253
CA $438 total
includes taxes & fees
Feb 10 - Feb 11
Modern, luxurious cabin in the woods - 21

Ocean Views and Modern Flair | New Renovation

Ocean Views and Modern Flair | New Renovation
Old Orchard Beach
The price is CA $121
CA $365 total
includes taxes & fees
Feb 10 - Feb 11
Ocean Views and Modern Flair | New Renovation

Clean cozy cottage 1 mile from beach.

Clean cozy cottage 1 mile from beach.
Old Orchard Beach
8.0 out of 10, Very good, (11 reviews)
"This house met all of our needs. It was updated and clean and has a nice little quiet enclosed back yard with a fire pit, grill and dining area. "
United States
Alyssa F.
The price is CA $176
CA $544 total
includes taxes & fees
Feb 10 - Feb 11
Clean cozy cottage 1 mile from beach.

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (25 reviews)
"Great host communication, arrival and access were easy, house was very clean and comfortable. Will definitely stay again and recommend to fellow Bowdoin families. House is in a great family neighborhood- enjoyed seeing how creative neighbors were with Halloween- would be a great place for kids! Close to town, Bowdoin and so much midcoast has to offer and explore! Thank you!"
United States
Alison O.
The price is CA $191
CA $535 total
includes taxes & fees
Feb 10 - Feb 11
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

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

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is CA $137
CA $295 total
includes taxes & fees
Feb 12 - Feb 13
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is CA $274
CA $531 total
includes taxes & fees
Feb 10 - Feb 11
Modern Getaway by the Sea

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is CA $217
CA $456 total
includes taxes & fees
Feb 11 - Feb 12
Modern & Sunny House Steps from the Promenade. Private Parking!

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (6 reviews)
"I loved that the hosts live nearby and responded quickly when we needed anything. Having a washer and dryer onsite is great for longer stays. Beds were comfortable and plenty of blankets and pillows. Highly recommend this property."
United States
Terry
The price is CA $149
CA $484 total
includes taxes & fees
Feb 19 - Feb 20
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is CA $114
CA $270 total
includes taxes & fees
Feb 10 - Feb 11
Peaceful & minutes from the Old Port with private parking

Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
10.0 out of 10, Exceptional, (4 reviews)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is CA $190
CA $979 total
includes taxes & fees
Feb 16 - Feb 17
Waterfront Access with Kayaks, Private Deck and a Firepit

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is CA $128
CA $251 total
includes taxes & fees
Feb 11 - Feb 12
Adorable Portland getaway on the Eastern Promenade

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (124 reviews)
"Great location for an our trip; laundry in basement "
United States
maria h.
The price is CA $172
CA $386 total
includes taxes & fees
Feb 10 - Feb 11
City Amenities, Casco Bay Sunrises and Natural Beauty

Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!

Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!
Pine Point
9.4 out of 10, Exceptional, (32 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is CA $145
CA $436 total
includes taxes & fees
Feb 11 - Feb 12
Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is CA $154
CA $294 total
includes taxes & fees
Feb 10 - Feb 11
Charming Studio apartment with WiFi, AC in welcoming Portland

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (6 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 $204
CA $420 total
includes taxes & fees
Feb 10 - Feb 11
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?

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port: This vacation home rental near Windham is located on a river and has a fireplace, a furnished patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 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.