Holiday Homes in Windham

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Windham and around

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (51)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is €262
includes taxes & fees
14 Sept - 15 Sept
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
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, (13)
"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
Summer Fun, Lake View, Firepit, Outdoor grilling, walk to the lake
Interior

Summer Fun, Lake View, Firepit, Outdoor grilling, walk to the lake

7.8 out of 10, Good, (11)
"Perfect location and communication with the property manager"
Summer Fun, Lake View, Firepit, Outdoor grilling, walk to the lake
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, (44)
"The house is in a wonderful location with great views of the ocean from several rooms. The listing photos really do tell the story of this beautiful home. The beach is just a few steps away from the property. Attention to detail was obviously put in to ensure a wonderful guest experience. The home is very clean, there are practical amenities throughout (4 smart TV’s), and our host was super communicative and accommodating. Portland & Saco being a short drive away is just icing on the cake. Can’t...
The price is €520
includes taxes & fees
15 Sept - 16 Sept
Beach House ∆ Prime Location ∆ Steps to the Ocean
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
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!
Fridge, microwave, oven, stovetop

Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

7.4 out of 10, Good, (10)
"Daughter lives in area it suited us just fine."
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!
Sunny Modern Oasis in Portland’s Trendy East End
Exterior detail

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (53)
"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"
Sunny Modern Oasis in Portland’s Trendy East End
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, (77)
"We had a great stay! Amazing weather and plenty of lobster."
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Beachfront, Just steps and you're on the beach!
On the beach

Beachfront, Just steps and you're on the beach!

10.0 out of 10, Exceptional, (2)
"Excellent cottage with great interior space and couldn’t ask for a better location. "
Beachfront, Just steps and you're on the beach!
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
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
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, (8)
The price is €1,833
includes taxes & fees
17 Aug - 18 Aug
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, ping pong, books

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very good, (55)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
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
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]
Marina

Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

9.6 out of 10, Exceptional, (15)
"Would stay here again. Loved the location and the size of the rooms! Perfect for a group and very pet friendly."
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]
Enchanting 3BR Farmhouse Retreat Nature Getaway
Fridge, microwave, oven, stovetop

Enchanting 3BR Farmhouse Retreat Nature Getaway

10.0 out of 10, Exceptional, (3)
"We really enjoyed this property. It was very clean, and very comfortable. We will visit again. "
Enchanting 3BR Farmhouse Retreat Nature Getaway
Spacious Lakehouse +Private Dock+Firepit+Kayaks
Outdoor dining

Spacious Lakehouse +Private Dock+Firepit+Kayaks

10.0 out of 10, Exceptional, (1)
"Perfect Lakefront Getaway on Panther PondWe had a fantastic week at this beautiful lake house on Panther Pond. The home was clean, spacious, and had a great kitchen.The lake was peaceful and perfect for swimming and kayaking. We spent most days on the water and evenings grilling and relaxing by the fire pit. One enjoyable perk was the ping pong table in the basement — we had nightly tournaments that kept us entertained.The location was quiet yet close to stores and towns like Raymond and...
Spacious Lakehouse +Private Dock+Firepit+Kayaks
Large, light filled 4 bedroom house - walk to ocean and ferry
Terrace/patio

Large, light filled 4 bedroom house - walk to ocean and ferry

10.0 out of 10, Exceptional, (33)
"Comfortable place to stay and enjoy time with family. We enjoyed exploring Peaks Island and Portland. Everything we needed."
Large, light filled 4 bedroom house - walk to ocean and ferry
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!
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 €873
includes taxes & fees
1 Sept - 2 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"I opted for the economy of the shared bath. It saved me a lot of money. I can't offer an opinion about the rooms with private baths. My room was very good. I will stay here again."
James 1-night trip
Posted 11 hours ago
Inn at St John Portland In-Town