North Windham Vacation Rentals from $101: Search Short-Term Rentals

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

1. Cozy Family Home w/ Beach Access

Raymond

$424 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

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

Gray

Matthew S.

$667 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

Raymond

$254 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

4. Portland 1-bedroom with enclosed porch & parking

Deering Center

Cricket C.

$99 nightly

Oct 22 - Oct 23

Total with taxes and fees

A rustic interior with a wooden dining table, bar stools, a sofa, and a television.

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

Standish

Alyssa

$279 nightly

Oct 22 - Oct 23

Total with taxes and fees

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

6. Great suburban location close to town!

Deering Center

Peter H.

$95 nightly

Oct 25 - Oct 26

Total with taxes and fees

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!

Standish

Alex D.

$264 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

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

Freeport

Rene B.

$396 nightly

Oct 28 - Oct 29

Total with taxes and fees

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

9. Studio Apartment near downtown Walkable!

West Bayside

Rose

$149 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

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

Westbrook

Bianca L.

$410 nightly

Oct 26 - Oct 27

Total with taxes and fees

A dirt path in a park with autumn foliage.

11. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

Westbrook

Genevieve W.

$577 nightly

Oct 22 - Oct 23

Total with taxes and fees

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.

$735 nightly

Oct 25 - Oct 26

Total with taxes and fees

A wooden staircase leading to a room with a white tiled wall and a door with a towel rack.

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

Casco

Edward R.

$277 nightly

Oct 22 - Oct 23

Total with taxes and fees

A bedroom with a large bed, white curtains, and a view through the windows.

14. Cozy 3BR | Pet Friendly | Near Portland | Parking

Westbrook

Angela B.

$440 nightly

Oct 25 - Oct 26

Total with taxes and fees

A compact kitchen with a refrigerator, microwave, and a small countertop.

15. Modern cabin w/ full bath | Hot tub add-on - 19

Freeport

Kim L.

$304 nightly

Oct 22 - Oct 23

Total with taxes and fees

A modern interior with a dining area, a living room, and a kitchen.

16. Studio Apartment in Freeport

Freeport

Susan S.

$150 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

17. The Weldon Hotel

Downtown Portland

Victoria

$284 nightly

Nov 17 - Nov 18

Total with taxes and fees

A cozy living room with a grey sofa, a wooden coffee table with a charcuterie board, and two glasses of white wine on a side table.

18. 2BR Apt | Full Kitchen | 10 Min to Old Port

Oakdale

"Our stay in Portland was great. Ride & Shine accommodations were great. The unit was clean and met our expectations, the location was perfect for us. We were able to explore the area in Portland. Rise & Shine hosts were great - their communication was great, they explained the check-in and check-out process and were attentive to our needs. We highly recommend others looking for a place to stay in Portland, ME."

Victor M.

$421 nightly

Oct 27 - Oct 28

Total with taxes and fees

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

19. Evalina Hotel

Downtown Portland

Rick

$402 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with a bar area, wooden ceiling, and skylights.

20. The Barnhouse with hot tub

New Gloucester

Jen V.

$326 nightly

Oct 26 - Oct 27

Total with taxes and fees

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Top North Windham Hotel Reviews

Grand Beach Inn

8/10 Good

"Nothing is better than an old motel directly across from the ocean. Off season staff hours appear to be nonexistent as my key was waiting in a mailbox. Getting a third floor corner room with no elevator nor view was a kick in butt. 6 or so corner rooms are situated in the corners where there isn't a view nor a balcony. Judging by the 10 or so cars in the lot, a lower level room or view was likely available."

Fireside Inn & Suites Portland

10/10 Excellent

"The staff is always very welcoming and pleasant. We had a small issue with our room (floor was wet near the ac unit) but staff on duty had us moved into an upgraded, newer room that was quite nice and had done so within a few minutes. Overall great place and we will visit again."

Clarion Pointe South Portland

10/10 Excellent

"Overall, I had a wonderful stay at this hotel! The breakfast was excellent, and the bed was incredibly comfortable — honestly, it was the most comfortable hotel bed I have ever slept in! The room was spacious, with plenty of room to relax and feel comfortable. The location was also very convenient, with cafés, gas stations, and other essential places nearby. Everything we needed was easily accessible. The only area that could use some improvement is housekeeping. The floor was not very clean, and there were a couple of hairs in the bathroom. Paying a little more attention to these details would make the experience even better. Despite this minor issue, I really enjoyed my stay. The hotel itself was great, and the comfortable bed, excellent breakfast, and convenient location made up for a lot. I would absolutely stay here again!"

Portland Harbor Hotel

10/10 Excellent

"Excellent, well-situated hotel. Front desk personnel were helpful and courteous. Sean and Simone were so kind in finding us the perfect room to suit our needs. Olivia at the bar in the evening was professional; we enjoyed our conversations with her. Great coffee-nook with perfect additions for a continental breakfast. Thanks to all who helped make our stay so enjoyable."

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit North Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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Check prices for these dates

Our top choices for North Windham vacation rentals

1. Cozy Family Home w/ Beach Access

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

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

4. Portland 1-bedroom with enclosed porch & parking

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

6. Great suburban location close to town!

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

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

9. Studio Apartment near downtown Walkable!

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

11. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

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. Cozy 3BR | Pet Friendly | Near Portland | Parking

15. Modern cabin w/ full bath | Hot tub add-on - 19

16. Studio Apartment in Freeport

17. The Weldon Hotel

18. 2BR Apt | Full Kitchen | 10 Min to Old Port

19. Evalina Hotel

20. The Barnhouse with hot tub

Find vacation rentals that suit your style

Top North Windham Hotel Reviews

Grand Beach Inn

Fireside Inn & Suites Portland

Spark by Hilton Portland Airport Maine Mall

Clarion Pointe South Portland

Clarion Hotel Portland Airport ME

Inn at St John Portland In-Town

Ramada Plaza by Wyndham Portland

Holiday Inn Portland-By the Bay by IHG

Portland Harbor Hotel

Find out more about North Windham

Frequently asked questions

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