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North Windham Vacation Rentals

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Our top choices for North Windham vacation 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 CA $212
CA $314 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $108
CA $261 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $310
CA $383 total
includes taxes & fees
Sep 17 - Sep 18
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 CA $208
CA $731 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $274
CA $1,092 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $211
CA $675 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $323
CA $394 total
includes taxes & fees
Sep 7 - Sep 8
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, (15 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 CA $303
CA $1,069 total
includes taxes & fees
Sep 9 - Sep 10
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.
The price is CA $353
CA $913 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $156
CA $413 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $221
CA $400 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $130
CA $229 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $557
CA $792 total
includes taxes & fees
Sep 5 - Sep 6
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 CA $241
CA $489 total
includes taxes & fees
Sep 5 - Sep 6
Cozy 1-bedroom cottage in soothing Standish with AC

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is CA $124
CA $154 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $221
CA $400 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $262
CA $511 total
includes taxes & fees
Sep 6 - Sep 7
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 CA $391
CA $810 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $193
CA $670 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $317
CA $559 total
includes taxes & fees
Sep 15 - Sep 16
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in North Windham?

Yes, there are vacation rentals close to well known points of interest in North Windham, or you can go with a more remote option if you'd like a relaxing place to stay. North Windham is known for its lake views.

What are some of the best vacation rentals in North Windham?

Charming 110-year former Inn 10' from the Ocean!: This vacation home rental near North Windham is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in North Windham?

Expedia has 13 vacation 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 larger area, you’ll find St Josephs College and Little Sebago Lake.

What’s a vacation rental in North Windham like?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in North Windham. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip.