Holiday Homes in Windham

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Windham

Our top choices for Windham holiday homes

4-bedroom vacation home steps to Old Orchard Beach Pier
Sun-loungers, beach towels

4-bedroom vacation home steps to Old Orchard Beach Pier

10.0 out of 10, Exceptional, (14)
"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"
4-bedroom vacation home steps to Old Orchard Beach Pier
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (55)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is AU$467
includes taxes & fees
14 Sept - 15 Sept
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Private kitchen

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

2.0 star property
9.0 out of 10, Wonderful, (9)
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
The Good Bones Abode
Property grounds

The Good Bones Abode

10.0 out of 10, Exceptional, (3)
"Beautiful older home with lots of character. Comfy beds, updated appliances, well manicured gardens and pretty outdoor sitting area. Close location to the interstate and urban areas, yet in a lovely country setting."
The Good Bones Abode
Spacious 4-bedroom house located in the heart of Portland, ME.
Interior

Spacious 4-bedroom house located in the heart of Portland, ME.

10.0 out of 10, Exceptional, (1)
"Clean, comfortable. "
The price is AU$1,383
includes taxes & fees
17 Sept - 18 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (78)
"We had a great stay! Amazing weather and plenty of lobster."
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Lakefront 3-bedroom, 2-bath house on Moose Pond in Denmark Maine with AC, WiFi
Property grounds

Lakefront 3-bedroom, 2-bath house on Moose Pond in Denmark Maine with AC, WiFi

9.6 out of 10, Exceptional, (5)
Lakefront 3-bedroom, 2-bath house on Moose Pond in Denmark Maine with AC, WiFi
Oceanside escape 🌊 perfect family getaway!
Terrace/patio

Oceanside escape 🌊 perfect family getaway!

9.8 out of 10, Exceptional, (18)
"Great location for proximity to Portland. Very clean and spacious."
Oceanside escape 🌊 perfect family getaway!
Modern Getaway by the Sea
Fridge, microwave, oven, stovetop

Modern Getaway by the Sea

The price is AU$899
includes taxes & fees
24 Aug - 25 Aug
Modern Getaway by the Sea
Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!
Fridge, microwave, oven, stovetop

Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!

10.0 out of 10, Exceptional, (62)
"Great stay!"
Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!
Gull's Nest by Bayley Vacation Rentals
Fridge, microwave, oven, stovetop

Gull's Nest by Bayley Vacation Rentals

Gull's Nest by Bayley Vacation Rentals
Shady Potts Point Cottage Cooled by Ocean Breezes
Terrace/patio

Shady Potts Point Cottage Cooled by Ocean Breezes

9.8 out of 10, Exceptional, (83)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes
Luxurious Penthouse with Modern Design in Downtown
Interior

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (12)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown
5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER
Dining

5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER

8.8 out of 10, Excellent, (6)
"Aucunes instructions de la part du proprio, clé, draps, serviettes. Nous avons dû chercher la clé longtemps. Manque de propreté, tapis sales, poussière, Proprio désagréable ."
5 HOUSES AWAY FROM BEACH - DISCOUNTED FOR 08/16-08/23,08/23-08/30 AND SEPTEMBER
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
Fridge, microwave, oven, stovetop

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

10.0 out of 10, Exceptional, (144)
"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (224)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel cot

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (45)
"Great location. House was clean. "
The price is AU$899
includes taxes & fees
15 Sept - 16 Sept
Beach House ∆ Prime Location ∆ Steps to the Ocean
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (95)
"Would love to stay here again!! "
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
The Moonglow! A beautiful ocean view house in Biddeford!
Terrace/patio

The Moonglow! A beautiful ocean view house in Biddeford!

9.8 out of 10, Exceptional, (117)
"House was beautiful! Comfy beds, amazing views,great location!"
The Moonglow! A beautiful ocean view house in Biddeford!
Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

8.0 out of 10, Very good, (1)
"Historic and charming home in a most interesting setting-- the community was a former military fort and barracks. Chat with neighbors on the front porch or watch wildlife and hang out in the backyard picnic tables. Comfortable beds and two full baths makes it good for group of 4-6 people. The golf cart is a godsend but there are bicycles and kayaks for land and water exploration. We didn't make it to the lovely looking pool or rec center for gym/bowling but they look like lots of fun. Rental and...
Elegant and efficient Island home 4 miles from downtown Portland
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

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

10/10 Excellent
"Good"
Jenny 1-night trip
Posted 20 hours ago
Days Inn by Wyndham Airport/Maine Mall