Windham Vacation Rentals

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Browse Select Windham Vacation Homes

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

9.6 out of 10, Exceptional, (73)
"Barry was a fabulous host. the house is a gem. I highly recommend it to future travelers to Maine."
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

The Moonglow! A beautiful ocean view house in Biddeford!

9.8 out of 10, Exceptional, (94)
"Gorgeous spot, great beach access. House was comfy and well-stocked. Great family get together!"
The Moonglow! A beautiful ocean view house in Biddeford!

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (38)
"The house is very clean, and it is only a minute walk to the beach. This was the second time we’ve stayed in this house and it won’t be the last! "
The price is CA $213
CA $708 total
includes taxes & fees
Jan 14 - Jan 15, 2025
Beach House ∆ Prime Location ∆ Steps to the Ocean

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Lakefront House

10.0 out of 10, Exceptional, (21)
" Thank you so much for sharing your lovely home with us. We had the perfect bachelorette weekend getaway! We would all definitely stay again! "
The price is CA $280
CA $1,110 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Lakefront House

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

8.8 out of 10, Excellent, (15)
"Convenient to walking to town , great restaurants in the area for breakfast & dinner, house was perfect, comfortable, well maintained great off street parking and had everything we could ever had needed."
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Modern, Luxury Lakefront Home on Crescent Lake, Maine

10.0 out of 10, Exceptional, (103)
"Well equipped and well maintained, very comfortable and peaceful. We had a great stay!"
Modern, Luxury Lakefront Home on Crescent Lake, Maine

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!

Immaculate Beachfront Retreat with Chef’s Kitchen, Ocean Vistas & Firepit

9.4 out of 10, Exceptional, (16)
"We had The Best Time here! The house was perfect – and just what we were looking for. Plenty of space for 9 people – never felt crowded or on top of each other. Having multiple living/hanging out spaces (inside and out) and 2 laundry rooms were great. Super special that we could all sit down to eat together at the big, long kitchen table. All the rooms and beds were so comfortable. Multiple AC units throughout the house was nice to let people adjust as per individual preference. The location was...
Immaculate Beachfront Retreat with Chef’s Kitchen, Ocean Vistas & Firepit

Surf Spry - Beach House in Saco Bay

9.8 out of 10, Exceptional, (16)
"The property is lovely. The location is perfect, as the ocean views are simply fantastic, but it was right in the middle of the places we tend to visit. If anything, the pictures do not do it justice. Waking up to the sunrise via a wall of windows was great. Highly recommend. "
Surf Spry - Beach House in Saco Bay

Sebago Lake Retreat with Private Beach

9.6 out of 10, Exceptional, (53)
"Despite poor weather, the week did not disappoint. Steve was quick to respond to an issue. The house sits in a quiet cove. Would definitely would return for a third visit."
Sebago Lake Retreat with Private Beach

NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!

10.0 out of 10, Exceptional, (48)
"Spacious and and private! My family always enjoys their visit to Maine but this home and the property really made this visit special. Communication throughout the booking and reservation was easy and all of our questions were answered promptly. Thank you!"
NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!

Sweet Maine Cottage in Camp Ellis

9.0 out of 10, Wonderful, (8)
"Great place, nice location"
Sweet Maine Cottage in Camp Ellis

Edgewater Retreat on Little Sebago Lake - Lakefront w/Sauna & EV Charger

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay in Gray. Thank you for helping us. Most of us were out kayaking on the lake/bay. The grand daughters enjoyed the kayaking and the swimming. the only complaint from everyone was that we had to depart for our return back to SC. You have a beautiful house. thank you for allowing us to visit."
Edgewater Retreat on Little Sebago Lake - Lakefront w/Sauna & EV Charger

"Loon Cottage" on Sand Pond

10.0 out of 10, Exceptional, (3)
"The cabin was very clean when we arrived. The beds were very comfortable. The cabin has everything you need including many things in the kitchen to make meals if you want to. Towels, sheets, blankets, and swim towels were also provided. We enjoyed using the paddle boards and paddle boats. The pond was great for swimming and boating. The cabin has windows on all sides so we enjoyed lots of fresh air. It was also very quiet, restful, and peaceful on the pond. "
"Loon Cottage" on Sand Pond

Point Sebago Gated Golf & Beach Community

10.0 out of 10, Exceptional, (3)
"The house was clean and well appointed. We would definitely stay here again!"
Point Sebago Gated Golf & Beach Community

beautiful home away from home in Orchard Beach

7.8 out of 10, Good, (9)
"Wonderful!..we all had our own comfy bedrooms…The kitchen was fully stocked with everything you might need..Loved the back porch with tv and couches..Big back yard with fire pit which we used twice.Ahmad even gave us the wood.Very clean…and the air conditioning was greatly appreciated.Ahmad was the perfect host. Warning…..owner has a dog on the premises if you’re bringing a pet…and watch out…the hot water is scalding!.If you’re looking for a vacation home near the beach but in a quiet area,this...
beautiful home away from home in Orchard Beach

Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

10.0 out of 10, Exceptional, (19)
"Our stay was memorable and so enjoyable. There were 5 of us, 4 adults and 1 child. The location is in a nice little neighborhood, only steps from Crescent Beach. We could sit on our deck and see the ocean and sleep by the sounds of the waves. This property has so much to offer with three bedrooms, one of which is downstairs for this older stair challenged lady. It has three parking spots and a lovely fenced yard for the kids to play in. The cottage was very clean and the owner has it stocked...
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (1)
"As you enter the house, you are entering the kitchen and looking at the most wall sized widow framed picturesque ocean waterfront view with islands included. We had two children with us and there was a has sack storage box filled with toys and a midsized toy kitchen that kept the children busy. The accommodations were cozy and homelike . We are already contemplating a warmer season return to enjoy the oceanfront amenities!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
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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Other property types in Windham

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

8.6 out of 10, Excellent, (35)
"We would absolutely book this house again. Super peaceful location. Loons in the morning were a stellar start to each day. "
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (38)
"The house is very clean, and it is only a minute walk to the beach. This was the second time we’ve stayed in this house and it won’t be the last! "
The price is CA $213
CA $708 total
includes taxes & fees
Jan 14 - Jan 15, 2025
Beach House ∆ Prime Location ∆ Steps to the Ocean
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.