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North Windham Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for North Windham vacation rentals

A dining area with a wooden table, two chairs, and a window with a view of trees.

1. Cozy 1 BR ADU | Private Access | Projector Theater

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (5 reviews)
"Very clean! Small space (no microwave) pet friendly and very accommodating to our travel needs!"
United States
Traci P.
The price is ￥18,318
￥76,939 total
includes taxes & fees
Oct 7 - Oct 8
Cozy 1 BR ADU | Private Access | Projector Theater
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

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 ￥26,687
￥118,570 total
includes taxes & fees
Nov 2 - Nov 3
Waterfront Access with Kayaks, Private Deck and a Firepit
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

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is ￥35,530
￥44,063 total
includes taxes & fees
Oct 11 - Oct 12
Cozy 2-bedroom house with shared beach access to Sebago Lake
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

4. 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 ￥36,951
￥45,440 total
includes taxes & fees
Oct 7 - Oct 8
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

5. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is ￥13,422
￥16,864 total
includes taxes & fees
Oct 18 - Oct 19
Great suburban location close to town!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

6. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"As expected."
United States
Lance
The price is ￥14,093
￥17,535 total
includes taxes & fees
Oct 13 - Oct 14
Portland 1-bedroom with enclosed porch & parking
A dirt path in a park with autumn foliage.

7. 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 ￥69,496
￥99,332 total
includes taxes & fees
Oct 7 - Oct 8
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A bedroom with a large bed, white curtains, and a view through the windows.

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

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is ￥24,634
￥69,193 total
includes taxes & fees
Oct 7 - Oct 8
Cozy 3BR | Pet Friendly | Near Portland | Parking
A multi-story house with a dock and a children's play area.

9. 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, (17 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is ￥31,582
￥118,649 total
includes taxes & fees
Nov 1 - Nov 2
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location, the hosts are very responsive and an absolute pleasure to work with. The home was clean, inviting and easy to check in."
United States
Bianca L.
The price is ￥31,006
￥75,622 total
includes taxes & fees
Oct 7 - Oct 8
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Living area

11. Pet-Friendly Glamping Vacations at this Waterfront Safari Tent in Naples, Maine

Pet-Friendly Glamping Vacations at this Waterfront Safari Tent in Naples, Maine
Naples
The price is ￥17,370
￥22,376 total
includes taxes & fees
Oct 15 - Oct 16
Pet-Friendly Glamping Vacations at this Waterfront Safari Tent in Naples, Maine
A living room with a sofa, armchairs, a coffee table, and a potted plant.

12. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is ￥15,335
￥29,624 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful 1st Floor Apartment & Amazing Shower
The Desert of Maine Welcome Center has lots of fun goodies (including campground merch!)

13. 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 ￥38,088
￥61,482 total
includes taxes & fees
Oct 8 - Oct 9
Modern cabin w/ full bath & kitchenette - 03
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

14. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is ￥12,435
￥23,773 total
includes taxes & fees
Nov 1 - Nov 2
Studio Apartment near downtown Walkable!
A cabin with a fire pit and outdoor seating.

15. 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 ￥25,439
￥45,457 total
includes taxes & fees
Oct 7 - Oct 8
Glamping cabin w/ full bath + spa access - 21
A modern kitchen with a bar area, wooden ceiling, and skylights.

16. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (10 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is ￥29,845
￥56,112 total
includes taxes & fees
Oct 7 - Oct 8
The Barnhouse with hot tub
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

17. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (27 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is ￥16,598
￥31,517 total
includes taxes & fees
Oct 28 - Oct 29
Bright & Spacious Apartment with Amazing Shower
A gym with treadmills, elliptical machines, and exercise balls.

18. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.2 out of 10, Wonderful, (20 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
The price is ￥18,160
￥23,237 total
includes taxes & fees
Nov 5 - Nov 6
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A multi-story building with a stone facade, large windows, and a corner entrance.

19. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (14 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is ￥54,319
￥82,895 total
includes taxes & fees
Nov 3 - Nov 4
Evalina Hotel
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

20. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (123 reviews)
"Really nice room and location"
United States
Victoria
The price is ￥32,385
￥47,139 total
includes taxes & fees
Nov 2 - Nov 3
The Weldon 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.
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Top North Windham Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"The inn itself was beautifully kept. The water pressure was great. There was plenty of hot water except very early in the morning (before 6am). I didn’t walk in the area but if I had too, I wouldn’t feel comfortable in the evening. There was parking behind the hotel and I was lucky to get a spot both nights that I was there otherwise you would have to park in their other lot somewhere around the corner. They had lemon water, fruit, cookies, tea and coffee out all the time. The included breakfast was just an easy grab a toasted bagel and go. Nothing special but it was a nice offer. The beds were soft, the AC worked well and our room was very large. Our room was on the second floor, no elevator and extremely steep steps, but staff was always available to help with bags or luggage. Overall, a very nice stay and less expensive than closer to town."
Jane 2-night trip
Posted 2 hours ago
Inn at St John Portland In-Town

Find out more about North Windham

Search for holiday rentals in North Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in North Windham using one of the methods below:

  • View our selection of featured holiday rentals in North Windham
  • Use the map to find apartments and other holiday homes in the North Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in North Windham while they last

Look no further and take a look at our great range of rental properties in North Windham!

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.