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 €298
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 €728
includes taxes & fees
28 Oct - 29 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 €562
includes taxes & fees
28 Oct - 29 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 €641
includes taxes & fees
31 Oct - 1 Nov
Gorgeous 3-bedroom house in charming Portland
A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

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 €421
includes taxes & fees
29 Oct - 30 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
Cozy 2-bedroom house with shared beach access to Sebago Lake
A beach with footprints, a person standing, and birds on the sand.

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 €303
includes taxes & fees
28 Oct - 29 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

8. 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 €985
includes taxes & fees
28 Oct - 29 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

9. 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 €326
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

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 €816
includes taxes & fees
1 Nov - 2 Nov
Luxe 5 Bed/ 3 Bath with Game Room & AC
Dining

11. 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 €1,452
includes taxes & fees
29 Oct - 30 Oct
ANY BIG PARTY!!!!
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

12. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €303
includes taxes & fees
28 Oct - 29 Oct
Quiet Spot in lovely Freeport neighborhood
Private kitchen

13. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space
Downtown Portland
Steps to Old Port, balcony, private outdoor space
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

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 €446
includes taxes & fees
28 Oct - 29 Oct
Modern & Sunny House Steps from the Promenade.
A wooden covered porch with a green door, potted plants, and a red watering can.

15. Charming West End Victorian

Charming West End Victorian
Parkside
The price is €652
includes taxes & fees
28 Oct - 29 Oct
Charming West End Victorian
A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

16. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (10 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
The price is €374
includes taxes & fees
11 Nov - 12 Nov
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A beach with clear water, a sandy shore, and a rocky outcrop with vegetation.

17. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is €462
includes taxes & fees
28 Oct - 29 Oct
Newly Remodeled Cottage with AC- Sebago Lake Area
A modern kitchen with a wooden dining table, a ceiling fan, and a view of the outdoors.

18. 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.
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
A building named Willard Square with a storefront and a red vehicle parked outside.

19. 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 €598
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home
A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

20. Whole Home | Sleeps 16 | Roof Deck|5 mins Downtown

Whole Home | Sleeps 16 | Roof Deck|5 mins 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.
Whole Home | Sleeps 16 | Roof Deck|5 mins Downtown
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
"Great hotel, great location. Staff was very helpful"
Staci 1-night trip
Posted 2 hours ago
Cambria Hotel Portland Downtown-Old Port

Find out more about Windham

Windham Holiday Homes information

Number of reviews
283
Accommodation
936 Holiday Homes
Lowest Price
€298
Highest Price
€1,452