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North Windham Holiday Rentals

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Our top choices for North Windham holiday rentals

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 NZ$385
includes taxes & fees
9 Sept - 10 Sept
Sebago Lake studio-style condo with enclosed sunroom and sunset views

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 NZ$322
includes taxes & fees
8 Sept - 9 Sept
Sebago Lake Cottage on Raymond Cape

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 NZ$467
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-bedroom house with shared beach access to Sebago Lake

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 NZ$871
includes taxes & fees
6 Oct - 7 Oct
Cozy 1 BR ADU | Private Access | Projector Theater

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 NZ$1,324
includes taxes & fees
30 Sept - 1 Oct
Waterfront Access with Kayaks, Private Deck and a Firepit

6. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is NZ$793
includes taxes & fees
7 Sept - 8 Sept
Cozy Family Home w/ Beach Access

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 NZ$491
includes taxes & fees
7 Sept - 8 Sept
THE LILLIPAD.Off-grid A frame. Sebago lake region!

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 NZ$1,310
includes taxes & fees
8 Sept - 9 Sept
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

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

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 NZ$504
includes taxes & fees
7 Sept - 8 Sept
Serenity between the lakes and seashore

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 NZ$492
includes taxes & fees
8 Sept - 9 Sept
Modern cabin w/ full bath & kitchenette - 03

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 NZ$283
includes taxes & fees
7 Sept - 8 Sept
Private Entrance Residential Portland

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 NZ$971
includes taxes & fees
7 Sept - 8 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

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

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
The price is NZ$586
includes taxes & fees
20 Sept - 21 Sept
Cozy 1-bedroom cottage in soothing Standish with AC

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
Great suburban location close to town!

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 NZ$492
includes taxes & fees
8 Sept - 9 Sept
Glamping cabin w/ full bath + spa access - 21

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 NZ$634
includes taxes & fees
13 Sept - 14 Sept
Fortland Island Campground

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 NZ$979
includes taxes & fees
7 Sept - 8 Sept
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

19. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is NZ$830
includes taxes & fees
7 Sept - 8 Sept
Fully Updated Airy Historic Home in South Freeport

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 NZ$696
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

Find out more about North Windham

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our North Windham holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up North Windham. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in North Windham. Seeing all the best attractions is bound to make you fall in love with North Windham. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in North Windham short-term rentals, that won’t be hard to do.

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.