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Vacation Homes in Windham

Serene 1-bedroom house in Windham with Babbling Brook

Windham
Serene 1-bedroom house in Windham with Babbling Brook

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
$151 nightly
The price is $164
Nov 16 - Nov 17
Total with taxes and fees
The Outlet Studio, Rustic Comfort w Fireplace

Mere Point Sunrise Views at Eastern Shore!

Brunswick
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
$374 nightly
The price is $378
Nov 16 - Nov 17
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
$322 nightly
The price is $351
Nov 17 - Nov 18
Total with taxes and fees
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (24)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
$285 nightly
The price is $311
Nov 29 - Nov 30
Total with taxes and fees
Serenity between the lakes and seashore

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

Old Orchard Beach
10.0 out of 10, Exceptional, (5)
"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
$349 nightly
The price is $353
Nov 16 - Nov 17
Total with taxes and fees
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Orchid Harbor, Bailey Island 3BR

Harpswell
9.8 out of 10, Exceptional, (7)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
United States
Jason M.
$411 nightly
The price is $415
Nov 24 - Nov 25
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay the weekend after Christmas. The home had absolutely everything we needed and was both comfortable and beautiful! Everything was clearly labeled and so easy settle in. Very close to the beach which was awesome to visit even in the winter!"
United States
Elizabeth M.
$443 nightly
The price is $483
Nov 16 - Nov 17
Total with taxes and fees
Beach House ∆ Prime Location ∆ Steps to the Ocean

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

Brunswick
8.8 out of 10, Excellent, (23)
"Great location for baileys island and popham"
United States
Anonymous traveler
$367 nightly
The price is $400
Nov 16 - Nov 17
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Upscale Spacious OOB Beach House - Seasonal Heated Pool

Old Orchard Beach
10.0 out of 10, Exceptional, (11)
"clean and comfortable. close to everything and had all we needed."
United States
mark g.
$436 nightly
The price is $476
Nov 17 - Nov 18
Total with taxes and fees
Upscale Spacious OOB Beach House - Seasonal Heated Pool

The Barnhouse with hot tub

New Gloucester
9.8 out of 10, Exceptional, (6)
"Clean, quiet, and comfortable respite from the bustle of the city. The property is well-stocked and welcoming. We had our own private outdoors area with a nice hot tub and seating area. Our family enjoyed our time at The Barnhouse. It was within driving distance to our various activities near the Portland coastal region."
United States
Lisa K.
$281 nightly
The price is $306
Nov 16 - Nov 17
Total with taxes and fees
The Barnhouse with hot tub

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland

Biddeford
10.0 out of 10, Exceptional, (8)
"We spent the days exploring the area (hikes, horseback riding, seeing lighthouses, exploring Portland etc.) and it was a nice place to come "home" to for my family (6 of us). We cooked a lot and the kitchen had everything we needed! It was a bit hotter while we were there (unseasonably I believe) and so we definitely used the window air conditioners. Overall the house was very comfortable for us, was clean and provided everything we needed! "
United States
Heidi K.
$558 nightly
The price is $608
Nov 18 - Nov 19
Total with taxes and fees
Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland

Spacious 5BR Family Dream with Private Beach Access

Old Orchard Beach
10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
United States
rebecca c.
$481 nightly
The price is $525
Nov 16 - Nov 17
Total with taxes and fees
Spacious 5BR Family Dream with Private Beach Access

Manor Suite,cozy newly renovated,downtown & beach

Bridgton
10.0 out of 10, Exceptional, (1)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
$151 nightly
The price is $164
Dec 2 - Dec 3
Total with taxes and fees
Manor Suite,cozy newly renovated,downtown & beach

Charming 1-bedroom ADU in wonderful Portland neighborhood

Back Cove
$210 nightly
The price is $229
Nov 16 - Nov 17
Total with taxes and fees
Charming 1-bedroom ADU in wonderful Portland neighborhood

Plush 5BR OOB Haven w/ Fire Pit

Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"We stayed for 3 nights and I can honestly say it was the cleanest place I ever stayed in Old Orchard Beach. The neighborhood was really quiet, so it was awesome for our little ones to go to sleep early. They had everything you could ever need for a trip, and more. The only complaint we have is the sink nasal spraying everywhere, which seemed to only be a water pressure issue, so no big deal at all. The host was very communicative for our upcoming trip. All things considered, we definitely will...
United States
Alex B.
$402 nightly
The price is $438
Nov 16 - Nov 17
Total with taxes and fees
Plush 5BR OOB Haven w/ Fire Pit

Classic New England Waterfront

Harpswell
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay! "
United States
Ashma B.
$651 nightly
The price is $710
Dec 1 - Dec 2
Total with taxes and fees
Classic New England Waterfront

5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

Casco
10.0 out of 10, Exceptional, (14)
"Great property, loved having 2 houses and extra fridge for Thanksgiving. Enough room for everyone to be together or find space. It was cold and snowed once, but we would love to try it in the summer."
United States
Lori H.
$688 nightly
The price is $696
Nov 16 - Nov 17
Total with taxes and fees
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach
9.4 out of 10, Exceptional, (14)
"The property was in a good location from everything available in the beach area and the house had enough space to accommodate all 12 of us."
United States
Wayne R.
$434 nightly
The price is $474
Nov 16 - Nov 17
Total with taxes and fees
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Spacious Portland Home + Parking

Parkside
9.0 out of 10, Wonderful, (2)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
$531 nightly
The price is $579
Nov 16 - Nov 17
Total with taxes and fees
Spacious Portland Home + Parking
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

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Windham Vacation Homes information

Number of reviews
184
Accommodation
919 Vacation Homes
Lowest Price
$164
Highest Price
$710

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