North Windham Holiday Rentals

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Holiday Rentals in North Windham

Sensational House on Sebago Lake, Raymond, ME

9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"Beautiful place , had everything you need . Very comfortable bed . Great shower & Kitchen . Also a great location! "
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (99)
"Property was as described, communication was easy and fast, property was clean, spacious, and felt homey. We will be back! "
The price is AU$816
includes taxes & fees
8 Dec - 9 Dec
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Cozy, Elegant and Bright 2 bed in the East End

9.6 out of 10, Exceptional, (35)
"Fabulous location for us as it’s just 1/2 block from our son’s apartment. So close to Casco Bay and the Portland Port area. Walkable to restaurants and shopping. Nice sunny apartment! "
The price is AU$568
includes taxes & fees
8 Dec - 9 Dec
Cozy, Elegant and Bright 2 bed in the East End

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

9.6 out of 10, Exceptional, (26)
"Repeat visit. Short walk to beach. Convenient to stores if you want to shop. Cottage comfortable. We’ll be back!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

Lakefront home with lovely lake views - one mile from the casino

9.8 out of 10, Exceptional, (41)
"This was the perfect location to get away for the weekend and celebrate my wife and I’s 10 year anniversary. The property was clean, private, and had great views being on the pond. The hot tub was an added bonus. I would definitely recommend this home and stay here again! "
Lakefront home with lovely lake views - one mile from the casino

Incredible Location! Heart of Old Port|Roomy Condo

10.0 out of 10, Exceptional, (23)
"Four friends (65+) met for our annual reunion. The unit was very centrally located to explore Old Port. It was clean, well equipped and we had excellent communication with property manager. Fabulous restaurants within easy walking distance, had a great time! Definitely would book again! 5 stars!"
Incredible Location! Heart of Old Port|Roomy Condo

Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals

10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

9.0 out of 10, Wonderful, (27)
"Cute place - makes very good use of the space. It was comfortable and very conveniently located to everything we wanted to do. We have a few suggestions but overall very happy, had a wonderful time, and the ultimate compliment - we look forward to staying there again. "
The price is AU$598
includes taxes & fees
1 Dec - 2 Dec
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is AU$478
includes taxes & fees
9 Dec - 10 Dec
Glorious getaway on Portland's Eastern Promenade.

Serenity between the lakes and seashore

9.8 out of 10, Exceptional, (15)
"Good location near lots of hiking and not far from Portland "
The price is AU$444
includes taxes & fees
13 Dec - 14 Dec
Serenity between the lakes and seashore

Lakefront House

10.0 out of 10, Exceptional, (21)
" Thank you so much for sharing your lovely home with us. We had the perfect bachelorette weekend getaway! We would all definitely stay again! "
The price is AU$1,265
includes taxes & fees
5 Dec - 6 Dec
Lakefront House

Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

8.0 out of 10, Very good, (14)
"This property is situated right on the lake. In the listing it is not clear that it comes stocked with almost everything you could possibly need including pots and pans and plates and toilet paper and towels towels..towels.embedding"
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

Romantic getaway for two Thanksgiving at Trickey pond early check in

10.0 out of 10, Exceptional, (291)
"A lovely conferable place"
Romantic getaway for two Thanksgiving at Trickey pond early check in

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (56)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is AU$654
includes taxes & fees
1 Dec - 2 Dec
Elegant condo - walk to Portland's best restaurants & Old Port

Beautiful oceanside Castle with private beach and seasonal swimming pool

10.0 out of 10, Exceptional, (35)
"It was a wonderful home for a birthday celebration with friends that wanted to experience Maine. The grounds were expansive with lovely water views. The host were very responsive."
Beautiful oceanside Castle with private beach and seasonal swimming pool

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (111)
"We were two couples (in our 60’s) in Portland for a couple days visiting. John’s place was wonderful! We had plenty of space for the four of us with room to spare. Very comfortable and relaxing. We absolutely LOVED the front porch/deck. Very spacious and an amazing view of the beach and ocean! Bathroom and kitchen were not “updated” but it’s a 110 year old home so we really didn’t mind - everything worked and that’s what’s important. The apartment is upstairs and John lives downstairs. ...
Charming 110-year former Inn 10' from the Ocean!

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

8.6 out of 10, Excellent, (35)
"We would absolutely book this house again. Super peaceful location. Loons in the morning were a stellar start to each day. "
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Rent a room in the gorgeous Holt House

8.2 out of 10, Very good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
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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Other types of properties in North Windham you may be interested in

La Quinta Inn & Suites by Wyndham Portland

2.5 star property
9.0 out of 10, Wonderful, (2111)
"We went up to Portland to see the Maine Celtics and this place was reasonable and convenient. The room was very nice, the accessible bathroom very large. Could have used a bit more vacuuming (some wrappers, somebody nail clipping - ew)"
The price is AU$137
includes taxes & fees
28 Nov - 29 Nov
La Quinta Inn & Suites by Wyndham Portland

Casco Bay Hotel, Ascend Hotel Collection

3.5 star property
8.4 out of 10, Very good, (2375)
"I like most everything about this place and have stayed several times. The only flaws: the rooms often smell very strongly of air freshener, including the pillows. Bring your own pillow! And there is often no dark roast k-cups. Bring your own dark roast K-cups. And finally, they used to have a wonderful coffee maker downstairs, but the machine has been broken for months. Now it's brewed ahead and can be weak. "
The price is AU$120
includes taxes & fees
11 Dec - 12 Dec
Casco Bay Hotel, Ascend Hotel Collection

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1476)
"Will absolutely be staying again"
The price is AU$273
includes taxes & fees
1 Dec - 2 Dec
Portland Harbor Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub: This holiday home rental outside of North Windham is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals will I find in North Windham?

Expedia has 8 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.