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

Windham Vacation Rentals

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Check prices for these dates

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

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 CA $346
CA $1,120 total
includes taxes & fees
Oct 28 - Oct 29
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 CA $624
CA $892 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $163
CA $466 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $551
CA $1,375 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $177
CA $482 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $318
CA $390 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $605
CA $1,174 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $1,147
CA $1,772 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $580
CA $1,428 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $306
CA $1,091 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $203
CA $681 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $486
CA $792 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $170
CA $537 total
includes taxes & fees
Oct 15 - Oct 16
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 CA $244
CA $742 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $447
CA $980 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $526
CA $938 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $319
CA $394 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $245
CA $788 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $425
CA $854 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $161
CA $548 total
includes taxes & fees
Oct 29 - Oct 30
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

8/10 Good
"Hotel is ok, but a bit worn down"
Paul 1-night trip
Posted less than an hour ago
Quality Inn & Suites South Portland

Find out more about Windham

Windham Vacation Homes information

Number of reviews
398
Accommodation
926 Vacation Homes
Lowest Price
CA $390
Highest Price
CA $1,772

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