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Windham Vacation Rentals & Homes - 40 Rentals Available

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40 Vacation rentals near Windham

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(7)

1 / 23

Gorham Log cabin - 3 miles away

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
“Overall the cottage was great. Supplied all the towels and sheets we needed. The kayaks and canoe were so much fun. Life jackets were perfect. I would just have to say the only bad thing was the water in the house smelled and tasted like sulfur....”
- Review left on 09/19/2016

$100

Very Good (7 reviews)

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from $100 / night

(2)

1 / 54

Sebago Cottage - 8 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We have been coming here for several years with our granddaughters and never tire of this lovely spot. The cottage is always immaculate, well stocked, and you can count on a pie to be waiting for you in the refrigerator. The owners, Bob and Marian...”
- Review left on 07/16/2016

$139

Excellent (2 reviews)

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from $139 / night

1 / 13

Standish House - 9.3 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children

from $357 / night

1 / 11

Yarmouth House - 11.4 miles away

  • 2
  • 4
  • Min stay varies
  • Child friendly

from $69 / night

(6)

1 / 13

Portland Condo - 12 miles away

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning
“Beautifully furnished and ideally located for walking the city of Portland or sitting and enjoying a serene view of Casco Bay. Restaurants, markets and touring opportunities are minutes away and very accessible by walking or biking. The complex owner...”
- Review left on 08/22/2016

$243

Very Good (6 reviews)

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from $243 / night

1 / 29

Raymond Lodge - 12.3 miles away

  • 8
  • 21
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children

from $858 / night

1 / 28

Raymond Cottage - 12.3 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children

from $300 / night

(8)

1 / 26

South Portland House - 13.5 miles away

  • 4
  • 11
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning

$195

Excellent (8 reviews)

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from $195 / night

(6)

1 / 29

South Portland House - 13.9 miles away

  • 3
  • 10
  • 3 nights min
  • Nearest beach 0.2 mi
  • Ask about children
  • Air conditioning
“This is the third year that we have stayed at this property. Our family comes from 3 states and 3 continents to stay here and the house accommodated all 10 of us comfortably. The owner is easy to work with. When the electronic lock quit working on...”
- Review left on 08/03/2015

$230

Very Good (6 reviews)

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from $230 / night

(2)

1 / 24

Scarborough House - 14.4 miles away

  • 5
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Spent the weekend at the unit closest to the water with 4 other couples and had a great time. The accomodations were awesome and the location was great. The pictures and the description are spot on. Everything was there that we needed...”
- Review left on 11/08/2016

$286

Excellent (2 reviews)

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from $286 / night

(5)

1 / 8

Freeport Cottage - 15.4 miles away

  • 3
  • 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
“Hands down the cutest nicest little place to stay! Excellent accomdations, quaint town. Loved it and will be booking again in the near future...”
- Review left on 06/13/2016

$300

Very Good (5 reviews)

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from $300 / night

(2)

1 / 12

Cape Elizabeth Cottage - 16.1 miles away

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Pet friendly
“The cottage was cute and comfortable, perfect for 2 people. The bed was great and the living room allowed us to relax with a beautiful view of the ocean. The neighbors were a bit close but we still felt great about the location. Only bad thing was...”
- Review left on 07/31/2012

$143

Very Good (2 reviews)

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from $143 / night

(6)

1 / 15

Cape Elizabeth House - 16.1 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Pet friendly
“This home is remarkable- it is fully updated with gorgeous furnishing, and has so many items for cleaning, toilet paper etc. that I have not found with rentals. The view to the ocean is amazing, and there are even binoculars to look at the boats...”
- Review left on 11/01/2016

$400

Very Good (6 reviews)

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from $400 / night

(1)

1 / 30

Scarborough House - 17.5 miles away

  • 6
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“A beautiful home for our family to come together and enjoy Maine. This house had everything. We sat on the porch with our morning coffee and enjoyed the marsh birds. Swam in the ocean. Enjoyed a family lobster dinner and watched the Olympics together...”
- Review left on 08/27/2016

$429

Excellent (1 reviews)

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from $429 / night

(8)

1 / 25

Scarborough House - 17.8 miles away

  • 5
  • 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
“This turned out to be a perfect place for our family gathering. While the fixtures are outdated they were clean and functional. The staff at the Hotel that checked us in was terrific, especially Anna! They supplied us with extra bedding and towels...”
- Review left on 07/26/2016

$375

Very Good (8 reviews)

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from $375 / night

1 / 15

Old Orchard Beach Condo - 18.3 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children

from $214 / night

(21)

1 / 11

Old Orchard Beach Apartment - 18.3 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“I just spent a week end at this lovely beach bungalow and enjoyed every second. The pictures on the site are exactly what you see upon arrival. The beach decor makes you feel at home the moment you step through the front door. The caretakers;...”
- Review left on 08/23/2016

$150

Very Good (21 reviews)

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from $150 / night

1 / 13

Waterboro House - 18.4 miles away

  • 5
  • 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children

from $275 / night

1 / 17

Old Orchard Beach Condo - 18.5 miles away

  • 2
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning

$100

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from $100 / night

(2)

1 / 6

Old Orchard Beach House - 18.5 miles away

  • 6
  • 23
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We lost our Dad in June of 2016 and had planned on taking him to Maine with us in July. So it was with heavy hearts we left for our trip. But the house was wonderful...plenty of room for everyone and right on the water. We found ourselves sharing...”
- Review left on 09/02/2016

$500

Average (2 reviews)

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from $500 / night

1 / 20

Old Orchard Beach House - 18.5 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning

from $240 / night

(10)

1 / 24

Waterboro House - 18.6 miles away

  • 3
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
“This house was a perfect summer getaway! Perfect for two families especially with kids! The kids enjoyed fishing on the dock, canoe and Kayak rides around the lake. No complaints!!! We had a great week...”
- Review left on 07/25/2016

$357

Very Good (10 reviews)

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from $357 / night

(10)

1 / 12

Old Orchard Beach Cottage - 18.8 miles away

  • 3
  • 10
  • 7 nights min
  • Ask about children
“Nous étions parfaitement bien situé et la maison était fort agréable! Par contre un lit simple de moins que mentionné dans l'annonce.Le porche était fantastique on y a passé tout notre temps en dehors de la fabuleuse plage. Une semaine fantastique...”
- Review left on 08/31/2016

$350

Excellent (10 reviews)

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from $350 / night

(5)

1 / 11

Old Orchard Beach Cottage - 18.8 miles away

  • 4
  • 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
“Great location, comfortable, easy access to every thing. The owner is very responsive. The parking is tight, but can be managed as long as your neighbor is willing to work with you...”
- Review left on 09/06/2016

$300

Very Good (5 reviews)

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from $300 / night

(7)

1 / 14

Old Orchard Beach Apartment - 18.9 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family and I had an absolutely fantastic time at your property this summer. We have rented both the 40 (2011) and 42 (2015) house rentals, both houses are terrific for our size family. Your properties really provide everything we need or could...”
- Review left on 08/13/2015

$125

Very Good (7 reviews)

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from $125 / night

(5)

1 / 19

Old Orchard Beach Cottage - 19.4 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“Perfect condo for my family. Nice and quiet location, easy walk to the beach. Great location for walking to Boardwalk or Ocean Park. Would have 5 stars if there was A/C; was a little warm, but perhaps that is the way it is in Maine. Great...”
- Review left on 08/21/2016

$132

Very Good (5 reviews)

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from $132 / night

(1)

1 / 10

Old Orchard Beach House - 19.5 miles away

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Pet friendly

$186

Excellent (1 reviews)

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from $186 / night

1 / 24

Old Orchard Beach House - 19.6 miles away

  • 3
  • 9
  • 7 nights min
  • Ask about children
  • Air conditioning

from $257 / night

1 / 16

Old Orchard Beach House - 19.7 miles away

  • 5
  • 13
  • 7 nights min
  • Ask about children

from $407 / night

1 / 14

Old Orchard Beach Cottage - 19.7 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

from $234 / night

(4)

1 / 14

Old Orchard Beach House - 19.8 miles away

  • 4
  • 13
  • 7 nights min
  • Ask about children
“We found the seastar to be conveniently located on the beach and near the center. The unit was clean and pleasant. I would suggest a few baking sheets and large bowls for the kitchenOur unit was on the second floor so we had an intercom....”
- Review left on 08/13/2016

$314

Very Good (4 reviews)

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from $314 / night

1 / 19

Old Orchard Beach House - 20.1 miles away

  • 2
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $186 / night

(2)

1 / 11

Saco House - 20.6 miles away

  • 5
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
“This property more than met our expectations-House was spacious, views spectacular.We had our family reunion and everyone wants to go back again. Easy rental agreement-house was clean, beds more than comfortable-close to all activities. We will...”
- Review left on 08/07/2016

$600

Excellent (2 reviews)

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from $600 / night

(8)

1 / 8

Saco Cottage - 20.6 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
“Wanted this year's vacation place to be "on the beach" and not a house with an "ocean view or "just minutes away from the beach".. This home was perfect and definitely THE spot! Loved everything! Only sorry we didn't stay for 2 weeks...”
- Review left on 09/08/2016

$214

Very Good (8 reviews)

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from $214 / night

(3)

1 / 16

Saco House - 20.6 miles away

  • 2
  • 6
  • 7 nights min
  • Ask about children
“Great cottage. Ideal location that is close to the beach and away from the noise. Truly a home away from home...”
- Review left on 08/25/2014

$214

Very Good (3 reviews)

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from $214 / night

(7)

1 / 6

Brunswick House - 21.5 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
“We have stayed in many places in Maine over the years, and this is one of our favorites. Far enough from town to be very peaceful, but close enough to run to the store or have dinner out, the location was perfect. Every morning we had coffee on the...”
- Review left on 08/28/2016

$243

Very Good (7 reviews)

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from $243 / night

(2)

1 / 8

Orrs Island Apartment - 21.5 miles away

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

$140

Excellent (2 reviews)

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from $140 / night

1 / 27

Saco House - 22.2 miles away

  • 5
  • 14
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $514 / night

1 / 21

Saco House - 22.2 miles away

  • 2
  • 7
  • 7 nights min
  • Ask about children

from $214 / night

(1)

1 / 9

Saco House - 22.3 miles away

  • 2
  • 5
  • 7 nights min
  • Ask about children
  • Pet friendly

$171

Average (1 reviews)

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from $171 / night