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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windham holiday homes

A house surrounded by trees and a body of water.

1. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is £509
includes taxes & fees
20 Nov - 21 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A modern kitchen with light blue cabinets, a large island, stainless steel appliances, and a hanging pendant light.

2. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is £581
includes taxes & fees
18 Nov - 19 Nov
New and Spacious Family Home Close to Sebago Lake
A modern kitchen with a large island, bar stools, and a view through large windows.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is £576
includes taxes & fees
30 Nov - 1 Dec
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

4. 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 £203
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake
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 £341
includes taxes & fees
15 Nov - 16 Nov
Cozy Family Home w/ Beach Access
A beach with a pier and a building in the background.

6. 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
7.6 out of 10, Good, (4 reviews)
"Overall all nice stay. Thank you"
United States
Hope T.
The price is £244
includes taxes & fees
18 Nov - 19 Nov
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.

7. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is £767
includes taxes & fees
16 Nov - 17 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A backyard with picnic tables and a red umbrella, overlooking a body of water with boats.

8. 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 £1,170
includes taxes & fees
26 Nov - 27 Nov
ANY BIG PARTY!!!!
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

9. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
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 £743
includes taxes & fees
17 Nov - 18 Nov
Heated Game Room, Coastal Maine Cape Sleeps 10
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

10. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is £262
includes taxes & fees
15 Nov - 16 Nov
Quiet Spot in lovely Freeport neighborhood
A staircase with wooden railings, two wooden chairs with cushions, a small table with a lamp, and a potted plant.

11. 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
The price is £346
includes taxes & fees
15 Nov - 16 Nov
Fully Updated Airy Historic Home in South Freeport
A backyard with a white wooden fence, a small bush, a white wicker bench, and a stone wall in the background.

12. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is £254
includes taxes & fees
16 Nov - 17 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A storefront with a sign reading 'LB KITCHEN' and a window display advertising 'MORNING THINGS COFFEE LUNCH BOWLS'.

13. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is £385
includes taxes & fees
15 Nov - 16 Nov
Modern & Sunny East End House.
An outdoor patio area with a wooden deck, a barbecue grill, and a seating arrangement.

14. 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 £221
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
A wooden picnic table with a bench, set on a grassy lawn.

15. 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 £466
includes taxes & fees
15 Nov - 16 Nov
Willard Square Family Home
A multi-story house with a dock and a children's play area.

16. 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, (19 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is £568
includes taxes & fees
15 Nov - 16 Nov
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
A wooden covered porch with a green door, potted plants, and a red watering can.

17. Charming West End Victorian

Charming West End Victorian
Parkside
The price is £521
includes taxes & fees
2 Dec - 3 Dec
Charming West End Victorian
Room

18. Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.2 out of 10, Wonderful, (5 reviews)
"The Manor Suite was cozy and charming. It was walking distance from restaurants and shops. I would have loved to stay longer to explore the area.I hope to stay there again if I return to Bridgton next summer."
United States
Jennifer
The price is £109
includes taxes & fees
16 Nov - 17 Nov
Manor Suite,cozy newly renovated,downtown & beach
A two-story house with a covered porch, a small shed, and a well-maintained lawn.

19. Old Orchard Beach Neighborhood Home

Old Orchard Beach Neighborhood Home
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Excellent stay at this property. House is very nice, well furnished and clean. Location is perfect for beach time and downtown activities. We had good times and communication with host was 10/10. thank you"
United States
charles t.
The price is £755
includes taxes & fees
26 Nov - 27 Nov
Old Orchard Beach Neighborhood Home
A kitchen with white cabinetry, a marble countertop, and a gas stove.

20. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is £627
includes taxes & fees
15 Nov - 16 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers."
Eric 2-night trip
Posted 9 hours ago
Portland Harbor Hotel

Find out more about Windham

Windham Holiday Homes information

Number of reviews
250
Accommodation
945 Holiday Homes
Lowest Price
£109
Highest Price
£1,170