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North Windham Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for North Windham holiday rentals

A lakeside deck with outdoor seating and a dock extending into the water.

1. Sebago Lake studio-style condo with enclosed sunroom and sunset views

Sebago Lake studio-style condo with enclosed sunroom and sunset views
Standish
9.0 out of 10, Wonderful, (12 reviews)
The price is AU$320
includes taxes & fees
9 Sept - 10 Sept
Sebago Lake studio-style condo with enclosed sunroom and sunset views
A small wooden cabin with a porch, surrounded by a well-maintained garden and outdoor seating area.

2. Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape
Raymond
10.0 out of 10, Exceptional, (53 reviews)
"Beautiful location and wonderful hosts. Made us feel right at home."
United States
Donna
The price is AU$268
includes taxes & fees
8 Sept - 9 Sept
Sebago Lake Cottage on Raymond Cape
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

3. 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 AU$385
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-bedroom house with shared beach access to Sebago Lake
A dining area with a wooden table, two chairs, and a window with a view of trees.

4. Cozy 1 BR ADU | Private Access | Projector Theater

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (4 reviews)
"Spotlessly clean, very comfortable bed. Quietly watched a deer just a few feet from me outside the property. Very peaceful."
United States
Anne T.
The price is AU$719
includes taxes & fees
6 Oct - 7 Oct
Cozy 1 BR ADU | Private Access | Projector Theater
A spacious kitchen with a large island, wooden beams, and a view of the outdoors.

5. Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
9.8 out of 10, Exceptional, (7 reviews)
"In frosty conditions the house was warm and comfortable. Jen was really responsive and welcoming, and the space was perfect."
United States
Matthew S.
The price is AU$1,072
includes taxes & fees
29 Sept - 30 Sept
Waterfront Access with Kayaks, Private Deck and a Firepit
A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

6. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is AU$637
includes taxes & fees
7 Sept - 8 Sept
Cozy Family Home w/ Beach Access
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

7. THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (16 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is AU$400
includes taxes & fees
7 Sept - 8 Sept
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A multi-story house with a dock and a children's play area.

8. 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)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is AU$1,090
includes taxes & fees
9 Sept - 10 Sept
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
A dining area with a table and chairs, large windows with a view of trees and water, and a candle on the table.

9. Lakefront-Swim-Kayak-FirePit-20min to Portland

Lakefront-Swim-Kayak-FirePit-20min to Portland
Gray
9.6 out of 10, Exceptional, (16 reviews)
"Loved the space and location. We had a beautiful time with friends!"
United States
Lydia T.
The price is AU$886
includes taxes & fees
7 Sept - 8 Sept
Lakefront-Swim-Kayak-FirePit-20min to Portland
A snow-covered landscape with a house and a tree.

10. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is AU$416
includes taxes & fees
7 Sept - 8 Sept
Serenity between the lakes and seashore
A cabin with two chairs facing a fire pit, surrounded by trees.

11. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is AU$376
includes taxes & fees
8 Sept - 9 Sept
Modern cabin w/ full bath & kitchenette - 03
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

12. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (11 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is AU$234
includes taxes & fees
7 Sept - 8 Sept
Private Entrance Residential Portland
A dirt path in a park with autumn foliage.

13. 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 AU$801
includes taxes & fees
7 Sept - 8 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A hallway with wooden beams, a hanging clothes rack, a stone-tiled floor, and a door leading to another room.

14. Cozy 1-bedroom cottage in soothing Standish with AC

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
The price is AU$476
includes taxes & fees
20 Sept - 21 Sept
Cozy 1-bedroom cottage in soothing Standish with AC
A loft-style room with a sofa, a small table, a skylight, and a kitchenette.

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is AU$158
includes taxes & fees
8 Sept - 9 Sept
Great suburban location close to town!
A cabin with a fire pit and outdoor seating.

16. Glamping cabin w/ full bath + spa access - 21

Glamping cabin w/ full bath + spa access - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is AU$401
includes taxes & fees
8 Sept - 9 Sept
Glamping cabin w/ full bath + spa access - 21
A yurt with a bed, a desk, and a view of the outdoors.

17. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is AU$517
includes taxes & fees
13 Sept - 14 Sept
Fortland Island Campground
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

18. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
The price is AU$804
includes taxes & fees
7 Sept - 8 Sept
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

19. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is AU$666
includes taxes & fees
7 Sept - 8 Sept
Fully Updated Airy Historic Home in South Freeport
A harbor with boats docked, a pier, and buildings in the background.

20. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay at Mat's place! Convenient location, very cute apartment with a lovely view of the water. Well equipped for a couple's weekend away. We appreciated the sharp knives for cooking and the comfy couch!"
United States
Charlotte B.
The price is AU$556
includes taxes & fees
14 Sept - 15 Sept
Casco Bay Vista
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 North Windham Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Clean and comfortable. Helpful staff."
Teresa 3-night trip
Posted less than an hour ago
Holiday Inn Portland-By the Bay by IHG

Find out more about North Windham

Everything you need to know about North Windham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the North Windham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Windham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

North Windham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Windham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Windham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Windham holiday rentals we have selected for you start as low as AU$248 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on North Windham rentals

At Expedia, we put the best North Windham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top North Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Windham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in North Windham?

Yes, there are holiday rentals close to the most popular sights in North Windham, or you can select a more secluded option if you're looking for a relaxing stay. North Windham is known for its lake views.

What are some of the best holiday rentals that North Windham has to offer?

Charming 110-year former Inn 10' from the Ocean!: This holiday home rental outside of North Windham is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in North Windham?

Expedia has 13 holiday rentals for your stay in North Windham.

What can I see and do in North Windham?

Sebago Lake and Sebago Lake Basin are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find St Josephs College and Little Sebago Lake.

What’s a holiday rental in North Windham like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in North Windham. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.