Search Vacation Homes in Windham

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Windham

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is AED 826
AED 1,694 total
includes taxes & fees
3 Sep - 4 Sep
Entire Modern Chic Home in Windham

Serene 1-bedroom house in Windham with Babbling Brook

The price is AED 517
AED 1,056 total
includes taxes & fees
11 Sep - 12 Sep
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 AED 386
AED 649 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 357
AED 898 total
includes taxes & fees
8 Sep - 9 Sep
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 AED 727
AED 2,158 total
includes taxes & fees
24 Sep - 25 Sep
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 AED 459
AED 837 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 386
AED 649 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 556
AED 690 total
includes taxes & fees
9 Sep - 10 Sep
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"
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 AED 551
AED 1,469 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 744
AED 1,315 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 670
AED 1,616 total
includes taxes & fees
3 Sep - 4 Sep
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...
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 AED 665
AED 1,597 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 633
AED 1,571 total
includes taxes & fees
15 Sep - 16 Sep
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 AED 694
AED 1,317 total
includes taxes & fees
4 Sep - 5 Sep
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 AED 1,062
AED 2,721 total
includes taxes & fees
28 Sep - 29 Sep
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 AED 551
AED 1,345 total
includes taxes & fees
4 Sep - 5 Sep
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 AED 632
AED 1,270 total
includes taxes & fees
18 Sep - 19 Sep
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (1)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews