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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windham holiday homes

A window with a view of a snowy landscape and bare trees.

1. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
9.4 out of 10, Exceptional, (3 reviews)
"Great location. Very nice place."
United States
Bernie G.
The price is AU$460
includes taxes & fees
30 Oct - 31 Oct
Tranquility between the Lakes & Sea
A dining area with a long wooden table, six chairs, and a bench. There are large windows with curtains, a plant, and a view into another room.

2. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is AU$1,137
includes taxes & fees
27 Oct - 28 Oct
New and Spacious Family Home Close to Sebago Lake
A dirt path in a park with autumn foliage.

3. 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 AU$903
includes taxes & fees
27 Oct - 28 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

4. Gorgeous 3-bedroom house in charming Portland

Gorgeous 3-bedroom house in charming Portland
North Deering
9.0 out of 10, Wonderful, (4 reviews)
"This place was exactly as it looks in the photos. Really conveniently located with good amenities."
United States
Bridget M.
The price is AU$1,021
includes taxes & fees
31 Oct - 1 Nov
Gorgeous 3-bedroom house in charming Portland
A modern kitchen with a dining area, a living room with a sofa, and a large window.

5. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
10.0 out of 10, Exceptional, (1 review)
"Nice, clean, good location.Would Recommend!"
United States
glen l.
The price is AU$643
includes taxes & fees
27 Oct - 28 Oct
Cozy Family Home w/ Beach Access
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

6. 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 AU$398
includes taxes & fees
21 Nov - 22 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake
A covered wooden deck with a view of a building's exterior.

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
7.4 out of 10, Good, (3 reviews)
"The property was unique, with lots of updates to the interior that met and even exceeded our needs (4 TV's!). New appliances and fully stocked with kitchen-ware. Plenty of towels and beds to indeed sleep 10 as described. The host has thought carefully about what you might need during your stay. Outdoor seating is plentiful so if the weather is good, you're all set for hanging out."
United States
Annette
The price is AU$472
includes taxes & fees
27 Oct - 28 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AU$464
includes taxes & fees
27 Oct - 28 Oct
Quiet Spot in lovely Freeport neighborhood
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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, (84 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is AU$1,567
includes taxes & fees
27 Oct - 28 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A room with a basketball hoop, a wooden table with chairs, a projector, and a washing machine.

10. 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, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is AU$1,266
includes taxes & fees
1 Nov - 2 Nov
Luxe 5 Bed/ 3 Bath with Game Room & AC
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

11. 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, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AU$513
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

12. 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 AU$2,273
includes taxes & fees
29 Oct - 30 Oct
ANY BIG PARTY!!!!
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

13. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport
A room with a large sliding glass door leading to a balcony with chairs and potted plants.

14. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (50 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$711
includes taxes & fees
1 Nov - 2 Nov
Modern & Sunny House Steps from the Promenade.
A modern kitchen with a wooden dining table, a ceiling fan, and a view of the outdoors.

15. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with sauna, 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 AU$429
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
A living room with a sofa, armchair, and coffee table, a kitchen with appliances, and a dining area with chairs.

16. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is AU$712
includes taxes & fees
1 Nov - 2 Nov
Newly Remodeled Cottage with AC- Sebago Lake Area
A deck with a grill, chairs, and a table.

17. • Quiet 3BR Home Close to Biddeford Beaches

• Quiet 3BR Home Close to Biddeford Beaches
Biddeford
6.0 out of 10, (1 review)
"This place was okay- it served our needs. A few complaints- generally a dingy smell throughout the house, felt damp. The bathroom shower curtain has no liner so the curtain itself was very moldy. The grass wasnt mowed so I worried about ticks. The water tasted a little musty too but maybe thats just a Maine thing? Also the communication was pretty terrible with both the vrbo host and the property management company and I had a lot of trouble contacting them and getting the receipts I needed....
United States
Ellen B.
The price is AU$770
includes taxes & fees
30 Oct - 31 Oct
• Quiet 3BR Home Close to Biddeford Beaches
A building named Willard Square with a storefront and a red vehicle parked outside.

18. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AU$935
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home
A wooden covered porch with a green door, potted plants, and a red watering can.

19. Charming West End Victorian

Charming West End Victorian
Parkside
The price is AU$1,032
includes taxes & fees
27 Oct - 28 Oct
Charming West End Victorian
A lakeside property with a dock, inflatable raft, and a house with a balcony.

20. 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, (17 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is AU$1,029
includes taxes & fees
27 Oct - 28 Oct
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Very efficient staff. Hotel easy for parking. Decent breakfast included. Quiet room and comfortable bed. Slept well."
Suzanne 2-night trip
Posted 4 hours ago
Tru by Hilton Portland Airport Area

Find out more about Windham

Windham Holiday Homes information

Number of reviews
291
Accommodation
936 Holiday Homes
Lowest Price
AU$398
Highest Price
AU$2,273