Windham Vacation Rentals

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Tonight
Nov 12 - Nov 13
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Nov 13 - Nov 14
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Windham

Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is ￥28,441
￥42,562 total
includes taxes & fees
Dec 7 - Dec 8
The Weldon Hotel
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Terrace/patio
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
9.8 out of 10, Exceptional, (124)
"House was beautiful! Comfy beds, amazing views,great location!"
United States
Katherine C.
The Moonglow! A beautiful ocean view house in Biddeford!
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Exterior
Romantic getaway for 2 PEAK fall foliage!!!

Romantic getaway for 2 PEAK fall foliage!!!

Naples
10.0 out of 10, Exceptional, (313)
"Place is beautiful and well crafted with a perfect nature setting"
United States
Ian
Romantic getaway for 2 PEAK fall foliage!!!
Exterior
Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape

Raymond
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
Smart TV
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Old Orchard Beach
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Outdoor dining
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"Made a great place for a business retreat. WiFi worked well and we had plenty of space to spread out."
United States
dan b.
The price is ￥92,282
￥191,603 total
includes taxes & fees
Nov 18 - Nov 19
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Fridge, microwave, oven, stovetop
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Saco
10.0 out of 10, Exceptional, (104)
"Such a beautiful home in an amazing location! "
United States
Michelle H.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Beach nearby
2 min walk to the beach. Pet friendly condo

2 min walk to the beach. Pet friendly condo

Old Orchard Beach
8.2 out of 10, Very Good, (41)
"Over all it was good, bathroom was off bedroom, not convenient for other guest staying on futon in living room. Backyard for dogs was very small, but enough space for the pups to do their duty. In all it worked for the few days we were there!"
United States
Cindy H.
2 min walk to the beach. Pet friendly condo
Exterior
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Raymond
7.8 out of 10, Good, (14)
"This was the perfect place for my boyfriend and I to spend a lovely, relaxing weekend. The cabin is super tiny but the view is spectacular and there are massive windows with screens so, even when you're inside, you get some outside magic. We spent hours around the fire pit and got to experience a huge thunderstorm over the lake with the windows wide open. We were even able to check in two hours early! A few things to note: this place is small — a single room, really — and the bed is a pullout...
United States
Rebecca S.
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very Good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is ￥12,132
￥23,194 total
includes taxes & fees
Nov 13 - Nov 14
In-town no frills 2 bedroom apt
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"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!"
United States
Anonymous traveler
The price is ￥10,515
￥21,577 total
includes taxes & fees
Nov 13 - Nov 14
Studio Unit Walkable Everywhere
Property grounds
Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Raymond
10.0 out of 10, Exceptional, (7)
"This was a fabulous property in perfect location. The house and grounds were amazing. It was a sensational week."
United States
Brian C.
Private Lakefront Estate with 180 Degree Views
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (166)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Beach
Little Miss Cottages - Two Bedroom Cottage

Little Miss Cottages - Two Bedroom Cottage

Old Orchard Beach
9.0 out of 10, Wonderful, (4)
"It was a very enjoyable weekend stay. Cottage was clean and comfortable. The water heater was a bit noisy as was the traffic noise at the front bedroom, but otherwise, could not have ask for more. Perfect access to beach. "
United States
Lynne M.
The price is ￥21,476
￥45,756 total
includes taxes & fees
Nov 16 - Nov 17
Little Miss Cottages - Two Bedroom Cottage
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Old Orchard Beach
9.8 out of 10, Exceptional, (224)
"The view off the deck was breathtaking "
United States
Raymond
The price is ￥26,961
￥52,225 total
includes taxes & fees
Nov 13 - Nov 14
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
On the beach, sun loungers
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Old Orchard Beach
9.8 out of 10, Exceptional, (44)
"Great house with lots of room for a big family. So close to the beach with great views. Great outdoor spaces as well! "
United States
Moria B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
2 bedrooms, WiFi, bed sheets
The Dollhouse

The Dollhouse

Old Orchard Beach
9.2 out of 10, Wonderful, (5)
"We had a great time! The place was exactly like the pictures. It was clean and had lots of amenities. My only suggestion would have more towels because we had five people and four bath towels. "
United States
Molly D.
The price is ￥69,327
￥115,197 total
includes taxes & fees
Nov 24 - Nov 25
The Dollhouse
Fridge, microwave, oven, stovetop
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Old Orchard Beach
9.8 out of 10, Exceptional, (64)
"My wife and I both enjoyed our stay and found the unit to be very cute, clean and comfortable. The owners were also quite nice and communicated very well whenever we reached out to them. We had a great stay!"
United States
Russell R.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Everything was great clean rooms clean common spaces staff was pleasant , but the room temperature was set at 71 and I couldn’t cool it any lower than 65 . 65 is way warmer than comfortable to try and sleep. My only other concern was parking , they had a convention of some sort going on so I had to use the over flow parking and that part wasn’t explained very well"
Paul 1-night trip
Posted 20 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Seacoast Adventure, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Windham is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Windham?

Expedia has 32 vacation rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake Basin and Jordan Bay.

What are vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.