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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windham vacation homes

A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

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 SAR 916
SAR 2,967 total
includes taxes & fees
28 Oct - 29 Oct
Windham Lakefront: Fire Pit and Modern Comforts
A dirt path in a park with autumn foliage.

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 SAR 1,652
SAR 2,362 total
includes taxes & fees
4 Oct - 5 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A window with a view of a snowy landscape and bare trees.

3. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is SAR 488
SAR 1,293 total
includes taxes & fees
14 Oct - 15 Oct
Tranquility between the Lakes & Sea
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

4. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is SAR 1,386
SAR 3,549 total
includes taxes & fees
6 Oct - 7 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

5. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is SAR 1,783
SAR 3,318 total
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

6. 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.
Gorgeous 3-bedroom house in charming Portland
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

7. 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 SAR 845
SAR 1,040 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 2-bedroom house with shared beach access to Sebago Lake
A beach with footprints, a person standing, and birds on the sand.

8. 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
8.0 out of 10, Very good, (2 reviews)
"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 traveler
The price is SAR 469
SAR 1,281 total
includes taxes & fees
6 Oct - 7 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.

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, (82 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is SAR 2,619
SAR 4,172 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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.
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, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is SAR 426
SAR 1,446 total
includes taxes & fees
2 Nov - 3 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Dining

12. Family, friends, Gathering

Family, friends, Gathering
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 SAR 2,704
SAR 6,172 total
includes taxes & fees
8 Oct - 9 Oct
Family, friends, Gathering
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

13. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
Quiet Spot in lovely Freeport neighborhood
A two-story house with a balcony, a covered patio, and a fenced yard.

14. 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, (109 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is SAR 1,393
SAR 2,484 total
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A brick building with a sign for 'Woodfired Bagels' and 'Espresso-Fast Foods - Sandwiches'.

15. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is SAR 1,126
SAR 1,919 total
includes taxes & fees
1 Nov - 2 Nov
Modern & Sunny House Steps from the Promenade.
A wooden deck with a grill area, overlooking a lake with trees in the background.

16. 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, (2 reviews)
"Beautiful setting! Wishing we could have stayed longer. Awesome communication with the host, cleanliness is impeccable. Would definitely stay here again."
United States
MaryAnn F.
The price is SAR 845
SAR 1,039 total
includes taxes & fees
5 Oct - 6 Oct
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
A living room with a sofa, armchairs, a coffee table, and a patterned rug.

17. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is SAR 1,112
SAR 1,916 total
includes taxes & fees
13 Oct - 14 Oct
Newly Remodeled Cottage with AC- Sebago Lake Area
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.

18. 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, (9 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.
Chic 3-bedroom house in Munjoy Hill with off-street parking.
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 SAR 1,126
SAR 2,269 total
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
Exterior

20. 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 SAR 920
SAR 1,134 total
includes taxes & fees
13 Oct - 14 Oct
Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

8/10 Good
"When we checked in the room was freezing (AC on in Oct!) and reeked of air freshener, which gotten into all the bedding and my clothes. I am allergic to fragrance as are many people."
Karen 1-night trip
Posted 1 hour ago
Clarion Hotel Portland Airport ME