A white church with a steeple and red accents, surrounded by autumn trees.

Holiday Homes in Windham

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Windham holiday homes

TV, offices

1. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.4 out of 10, Exceptional, (3 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is €625
includes taxes & fees
30 Sept - 1 Oct
Windham Lakefront: Fire Pit and Modern Comforts
Property grounds

2. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is €502
includes taxes & fees
17 Sept - 18 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Dining

3. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is €769
includes taxes & fees
13 Sept - 14 Sept
New and Spacious Family Home Close to Sebago Lake
Interior

4. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is €290
includes taxes & fees
13 Sept - 14 Sept
Tranquility between the Lakes & Sea
Smart TV, fireplace

5. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is €238
includes taxes & fees
22 Sept - 23 Sept
Cozy 2-bedroom house with shared beach access to Sebago Lake
Smart TV

6. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is €878
includes taxes & fees
13 Sept - 14 Sept
Luxe 5 Bed/ 3 Bath with Game Room & AC
Beach

7. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
6.0 out of 10, (1 review)
"Place was clean and cozy. Big yard for games and a fire pit for s’mores. Based on previous review I brought pots/pans but didn’t need them. Everything was available. Stove is gas and I was not familiar with using one so that was the only “challenge”We had a ball and the place was perfect for us!!"
United States
Anonymous traveller
The price is €322
includes taxes & fees
13 Sept - 14 Sept
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Private kitchen

8. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is €286
includes taxes & fees
13 Sept - 14 Sept
Newly Remodeled Cottage with AC- Sebago Lake Area
Exterior detail

9. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is €1,034
includes taxes & fees
14 Sept - 15 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Exterior

10. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (16 reviews)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is €698
includes taxes & fees
13 Sept - 14 Sept
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Coffee/tea maker, fridge, microwave, dishwasher

11. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is €356
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in lovely Freeport desert pines neighborhood
TV, fireplace, offices

12. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
Fully Updated Lake View Home on Thomas Pond
Outdoor dining

13. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The Globe House on Munjoy Hill - Walk to Breweries
Terrace/patio

14. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Casco
10.0 out of 10, Exceptional, (1 review)
"An adorable little getaway on the cutest little lake. It is quiet and peaceful."
United States
E Tyler B.
The price is €238
includes taxes & fees
22 Sept - 23 Sept
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Interior

15. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Exterior

16. Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is €259
includes taxes & fees
22 Sept - 23 Sept
Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
Exterior

17. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home
Interior

18. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Oakdale
10.0 out of 10, Exceptional, (1 review)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
United States
Andy W.
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Outdoor dining

19. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
Modern & Sunny House Steps from the Promenade.
Dining

20. ANY BIG PARTY!!!!

ANY BIG PARTY!!!!
Standish
8.0 out of 10, Very good, (2 reviews)
"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."
United States
Logan R.
The price is €1,375
includes taxes & fees
17 Sept - 18 Sept
ANY BIG PARTY!!!!
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

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent
"clean. large room. good location. we really enjoyed."
muneyoshi 3-night trip
Posted less than an hour ago
Cambria Hotel Portland Downtown-Old Port

Find out more about Windham

Windham Holiday Homes information

Number of reviews
372
Accommodation
936 Holiday Homes
Lowest Price
€238
Highest Price
€1,375