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Vacation Homes in Windham

Our top choices for Windham vacation homes

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is ¥33,311
¥68,745 total
includes taxes & fees
Sep 9 - Sep 10
Entire Modern Chic Home in Windham

Serene 1-bedroom house in Windham with Babbling Brook

The price is ¥20,845
¥42,570 total
includes taxes & fees
Sep 16 - Sep 17
Serene 1-bedroom house in Windham with Babbling Brook

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is ¥15,545
¥26,498 total
includes taxes & fees
Sep 8 - Sep 9
Private Entrance Residential Portland

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is ¥17,428
¥39,329 total
includes taxes & fees
Sep 29 - Sep 30
Willard Beach–Private Apt Near Portland & Parks

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
The price is ¥29,395
¥87,383 total
includes taxes & fees
Sep 24 - Sep 25
30 Acres with Woodland Trails and Playground

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is ¥18,506
¥33,888 total
includes taxes & fees
Sep 14 - Sep 15
Charming Studio apartment with WiFi, AC in welcoming Portland

Studio Unit Walkable Everywhere

8.0 out of 10, Very Good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is ¥15,545
¥26,498 total
includes taxes & fees
Sep 8 - Sep 9
Studio Unit Walkable Everywhere

THE LILLIPAD.Off-grid A frame. Sebago lake region!

10.0 out of 10, Exceptional, (2)
"Charming cabin. Well maintained. Loved my stay! Highly recommend."
The price is ¥22,466
¥27,886 total
includes taxes & fees
Sep 9 - Sep 10
THE LILLIPAD.Off-grid A frame. Sebago lake region!

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is ¥22,603
¥51,014 total
includes taxes & fees
Sep 7 - Sep 8
Sauna & fire table near Portland's Back Cove

Bright 3 bedroom located in the heart of OOB

9.0 out of 10, Wonderful, (4)
"Perfect for our needs. Pictures don't do it justice, it is roomier than it looks. Would definitely book it again. "
The price is ¥22,208
¥59,548 total
includes taxes & fees
Sep 8 - Sep 9
Bright 3 bedroom located in the heart of OOB

Full sized home

9.8 out of 10, Exceptional, (37)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is ¥29,980
¥54,626 total
includes taxes & fees
Sep 15 - Sep 16
Full sized home

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (4)
"GoodLocation, very clean. Would stay again "
The price is ¥38,694
¥80,099 total
includes taxes & fees
Sep 14 - Sep 15
Luxury on Back Cove - Three Gables

Cozy Motel Stay – 2 Full Beds, Pool & Free Parking

8.0 out of 10, Very Good, (2)
"First, the good, the inside of our room was nice. We had two beds, a fridge, microwave, table and chairs and a tv. There was room to walk around. Now, the bad, upon arrival (after the 4pm check in time) there were trash bags lined up in front of our room. The housekeeper (Anne) was rude. The beds only had sheets and when asking housekeeper about blankets she rudely replied “well at least your room is clean”. She did bring the blankets a little later. There was a fenced in outside area (dirt...
The price is ¥14,698
¥23,563 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Motel Stay – 2 Full Beds, Pool & Free Parking

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

10.0 out of 10, Exceptional, (4)
"Very clean "
The price is ¥28,504
¥67,007 total
includes taxes & fees
Sep 24 - Sep 25
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (3)
"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."
The price is ¥26,627
¥64,628 total
includes taxes & fees
Sep 15 - Sep 16
Orchid Harbor, Bailey Island 3BR

The Barnhouse with hot tub

10.0 out of 10, Exceptional, (3)
"Thank you Bethany for a most wonderful stay. What a beautiful property you have here. We really loved the opportunity to enjoy the barn house. Hope you and your family have an awesome summer. "
The price is ¥27,981
¥51,478 total
includes taxes & fees
Oct 1 - Oct 2
The Barnhouse with hot tub

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
The price is ¥39,381
¥105,499 total
includes taxes & fees
Sep 15 - Sep 16
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

9.4 out of 10, Exceptional, (3)
"This space was fresh and clean, and close to everything.Check in and out was easy. We enjoyed our stay."
The price is ¥22,208
¥54,222 total
includes taxes & fees
Sep 5 - Sep 6
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (56)
"Quiet neighborhood. Nice place"
The price is ¥20,364
¥44,789 total
includes taxes & fees
Sep 18 - Sep 19
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (2)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
The price is ¥44,415
¥76,976 total
includes taxes & fees
Sep 16 - Sep 17
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
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

Find out more about Windham

Windham Vacation Homes information

Number of reviews
Accommodation
1004 Vacation Homes
Lowest Price
¥28,448
Highest Price
¥118,292