North Windham Vacation Rentals from CA $83: Short-Term Rentals for 2026

Q: 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.

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Our top choices for North Windham vacation rentals

A spacious kitchen with a large island, wooden beams, and a view of the outdoors.

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

Gray

Beth L.

A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

2. Cozy Family Home w/ Beach Access

Raymond

glen l.

A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

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

Standish

Alex D.

CA $388 total

includes taxes & fees

Nov 9 - Nov 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

Raymond

CA $359 total

includes taxes & fees

Nov 18 - Nov 19

A dining area with a long wooden table, six chairs, and a bench. There are large windows with curtains, a plant, and a view into another room.

5. New and Spacious Family Home Close to Sebago Lake

Standish

CA $1,052 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

6. The Weldon Hotel

Downtown Portland

Victoria

CA $395 total

includes taxes & fees

Dec 2 - Dec 3

A multi-story building with a stone facade, large windows, and a corner entrance.

7. Evalina Hotel

Downtown Portland

Eric

CA $575 total

includes taxes & fees

Dec 7 - Dec 8

A beach with clear water, a sandy shore, and a rocky outcrop with vegetation.

8. Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

A cabin with two chairs facing a fire pit, surrounded by trees.

9. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Freeport

Kirt v.

CA $418 total

includes taxes & fees

Nov 9 - Nov 10

A room with a leather armchair, ottoman, wooden cabinet with decorative items, and a television mounted on the wall.

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

Standish

Alyssa

CA $410 total

includes taxes & fees

Nov 29 - Nov 30

A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

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

Westbrook

Bianca L.

CA $613 total

includes taxes & fees

Nov 9 - Nov 10

A multi-story house with a dock and a children's play area.

12. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Casco

loie H.

CA $1,062 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with a wooden dining table, a ceiling fan, and a view of the outdoors.

13. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Casco

Edward R.

CA $391 total

includes taxes & fees

Nov 18 - Nov 19

A modern cabin with a large glass facade, a hot tub, and wooden steps leading to the entrance.

14. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

Naples

Gina P.

CA $1,042 total

includes taxes & fees

Nov 15 - Nov 16

A geodesic dome structure in a forest setting with a visible interior space.

15. Modern dome w/ full bath | Hot tub add-on - 04

Freeport

Rene B.

CA $632 total

includes taxes & fees

Nov 10 - Nov 11

A backyard with a wooden deck, a small staircase, and a wooden fence.

16. Great suburban location close to town!

Deering Center

Kaley

CA $110 total

includes taxes & fees

Nov 9 - Nov 10

A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

17. Portland 1-bedroom with enclosed porch & parking

Deering Center

Cricket C.

CA $115 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a coffee table with books.

18. Fully Updated Lake View Home on Thomas Pond

Casco

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

19. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

CA $1,111 total

includes taxes & fees

Nov 9 - Nov 10

20. Family, friends, Gathering

Standish

Logan R.

CA $2,199 total

includes taxes & fees

Nov 19 - Nov 20

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Top North Windham Hotel Reviews

A spacious lobby with multiple seating areas, a fireplace, and large windows.

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Suke Diadibwa

A breakfast area with a sign that reads "HAPPY BREAKFAST STARTS HERE" and a coffee machine.

Hampton Inn & Suites Portland West

Nasons Corner

10/10 Excellent

Mark

A hotel reception area with a wooden reception desk, a colorful abstract wall art, and a view of the outdoor area through a window.

Spark by Hilton Freeport

Freeport

10/10 Excellent

Sophie

A modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Nicole Emily Elizabeth

A hotel room with a bed, bedside table, TV, and a kitchenette in the background.

Holiday Inn Express Hotel & Suites South Portland by IHG

South Portland

10/10 Excellent

Joanne

A hotel with a large entrance, stone pillars, and a sign reading "Homewood Suites Hilton".

Homewood Suites by Hilton Portland

Scarborough

10/10 Excellent

Jamie

A two-story building with a large glass conservatory and yellow umbrellas in the garden area.

The Harraseeket Inn & Event House Freeport Downtown

Freeport

10/10 Excellent

Aaron

A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

10/10 Excellent

Stephane

A fire pit surrounded by wicker chairs in a garden setting.

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Barbara

Find out more about North Windham

Everything you need to know about North Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the North Windham vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

North Windham vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Windham vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Windham vacation rentals we have selected for you start as low as CA $83 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on North Windham rentals

At Expedia, we put the best North Windham vacation 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 vacation.

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 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.

North Windham Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for North Windham vacation rentals

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

2. Cozy Family Home w/ Beach Access

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

4. Cozy 2-bedroom house with shared beach access to Sebago Lake

5. New and Spacious Family Home Close to Sebago Lake

6. The Weldon Hotel

7. Evalina Hotel

8. Newly Remodeled Cottage with AC- Sebago Lake Area

9. Cabin w/ bath + kitchenette | Hot tub add-on - 03

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

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

12. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

13. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

14. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

15. Modern dome w/ full bath | Hot tub add-on - 04

16. Great suburban location close to town!

17. Portland 1-bedroom with enclosed porch & parking

18. Fully Updated Lake View Home on Thomas Pond

19. Newly Renovated Luxury House with Game Room

20. Family, friends, Gathering

Find vacation rentals that suit your style

Top North Windham Hotel Reviews

Embassy Suites by Hilton Portland Maine

10/10 Excellent

Find out more about North Windham

North Windham vacation rentals: An excellent choice for every season

How to find incredible deals on North Windham rentals

Frequently Asked Questions

Can I find vacation rentals in North Windham?

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

How many vacation rentals will I find in North Windham?

What can I see and do in North Windham?

What’s a vacation rental in North Windham like?