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 holiday 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 £585
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 £474
includes taxes & fees
1 Oct - 2 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 £246
includes taxes & fees
5 Oct - 6 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 £724
includes taxes & fees
6 Oct - 7 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A beach with footprints, a person standing, and birds on the sand.

5. 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 traveller
The price is £263
includes taxes & fees
6 Oct - 7 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
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 £208
includes taxes & fees
13 Oct - 14 Oct
Cozy 2-bedroom house with shared beach access to Sebago Lake
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

7. 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 £686
includes taxes & fees
5 Oct - 6 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
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, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is £921
includes taxes & fees
6 Oct - 7 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.

9. 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 £764
includes taxes & fees
1 Oct - 2 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
A multi-story house with a dock and a children's play area.

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)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is £572
includes taxes & fees
14 Oct - 15 Oct
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a coffee table with books.

11. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
The price is £405
includes taxes & fees
4 Oct - 5 Oct
Fully Updated Lake View Home on Thomas Pond
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

12. 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 £427
includes taxes & fees
13 Oct - 14 Oct
Modern & Sunny House Steps from the Promenade.
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
The price is £279
includes taxes & fees
12 Oct - 13 Oct
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

14. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is £388
includes taxes & fees
1 Oct - 2 Oct
Fully Updated Airy Historic Home in South Freeport
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

15. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is £522
includes taxes & fees
1 Oct - 2 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A two-story house with a balcony, a covered patio, and a fenced yard.

16. 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 £491
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A wooden deck with a grill area, overlooking a lake with trees in the background.

17. 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 £211
includes taxes & fees
12 Oct - 13 Oct
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
A living room with a grey sofa, two patterned armchairs, a round wicker coffee table, and a flat-screen TV mounted on the wall.

18. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
9.0 out of 10, Wonderful, (2 reviews)
"The location was very convenient. Easy drive to downtown Saco and Biddeford. As well as very quick access to the highway so Portland and other points are easy to get to. Ample parking."
United States
Ellen L.
The price is £437
includes taxes & fees
4 Oct - 5 Oct
Huge New Townhome 10mins from the Beach
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 £454
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

20. 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 £294
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

10/10 Excellent
"This is a very nice property and very clean. Staff were cordial. The hvac system worked well and wasn’t noisy. Room was clean. The room could have used a chair though. There was an office chair at the desk but the back wasn’t stable."
Robert 5-night trip
Posted 5 hours ago
Quality Inn & Suites South Portland

Find out more about Windham

Windham Holiday Homes information

Number of reviews
398
Accommodation
945 Holiday Homes
Lowest Price
£208
Highest Price
£921