North Windham Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for North Windham vacation rentals

2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 09

Large, luxurious geodesic dome - 09
Freeport
The price is ￥32,174
￥55,164 total
includes taxes & fees
Mar 30 - Mar 31
Large, luxurious geodesic dome - 09
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 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 ￥10,100
￥21,610 total
includes taxes & fees
Mar 30 - Mar 31
Private Entrance Residential Portland
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is ￥32,174
￥53,067 total
includes taxes & fees
Mar 30 - Mar 31
Large, luxurious geodesic dome - 04
Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (127 reviews)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is ￥17,313
￥41,587 total
includes taxes & fees
Mar 30 - Mar 31
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is ￥13,218
￥29,435 total
includes taxes & fees
Mar 30 - Mar 31
Sunny Spot with Private Parking.
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (28 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is ￥18,035
￥38,531 total
includes taxes & fees
Mar 30 - Mar 31
Pine Point Beach private, quaint, charming studio.
Desk, laptop workspace, free WiFi

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.6 out of 10, Exceptional, (12 reviews)
"The room was spotless. The hotel was very clean and the staff was very friendly and helpful."
United States
Monique
The price is ￥16,833
￥18,348 total
includes taxes & fees
Mar 31 - Apr 1
HomeAwhile
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (8 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is ￥20,359
￥40,189 total
includes taxes & fees
Apr 5 - Apr 6
Peaceful & minutes from the Old Port with private parking
Interior

Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"I could not have ask for a better place to stay for my winter holiday trip in Freeport, Maine. This studio apartment went above my expectations. The entire space was much larger than I thought it would be. From the entry downstairs & throughout the entire apartment, it was clean & well-kept. Kitchen is fully equipped, has adequate space for meal prep, and there is plenty of room around the table & kitchen counter for dining. The living room is a welcoming pleasant area, and there is ample space...
United States
Di W.
The price is ￥10,260
￥24,297 total
includes taxes & fees
Apr 6 - Apr 7
Studio Apartment in Freeport
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is ￥18,035
￥34,512 total
includes taxes & fees
Mar 30 - Mar 31
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (32 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
The price is ￥33,354
￥57,046 total
includes taxes & fees
Apr 9 - Apr 10
East end. Walk to food, beer and downtown fun.
Beach nearby, sun loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Trolley Access

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Trolley Access
Pine Point
9.6 out of 10, Exceptional, (35 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is ￥15,294
￥48,998 total
includes taxes & fees
Mar 31 - Apr 1
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Trolley Access
Exterior detail

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (77 reviews)
"Location was great. Parking was easy."
United States
Bruce G.
The price is ￥25,650
￥80,798 total
includes taxes & fees
Mar 30 - Mar 31
Elegant condo - walk to Portland's best restaurants & Old Port
Interior

Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (26 reviews)
"Great place. Had everything we needed and close to everything."
United States
Bill P.
The price is ￥18,179
￥52,666 total
includes taxes & fees
Mar 30 - Mar 31
Skyline 138: Charming West End Mansard Penthouse
Dining

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.4 out of 10, Exceptional, (3 reviews)
"All was great...clean and convenient."
United States
Krista P.
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
Interior

Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (54 reviews)
"Host was very welcoming and the place exceeded expectations! Made our stay better than we could have imagined!"
United States
Robert D.
The price is ￥19,486
￥39,238 total
includes taxes & fees
Mar 30 - Mar 31
Historic Home in the West End. Private Parking.
Exterior detail

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (129 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is ￥18,917
￥34,599 total
includes taxes & fees
Apr 1 - Apr 2
Adorable Portland getaway on the Eastern Promenade
On the beach, sun loungers, beach towels

Step right out to the beach! Amazing location 7 min to Portland.

Step right out to the beach! Amazing location 7 min to Portland.
Willard
10.0 out of 10, Exceptional, (13 reviews)
"The apartment was very clean and well appointed with everything you might need. The host was very friendly and attentive and check in and check out were very simple. Any questions I had were answered promptly. I would definitely stay here again!"
United States
Diana T.
The price is ￥23,886
￥69,720 total
includes taxes & fees
Mar 30 - Mar 31
Step right out to the beach! Amazing location 7 min to Portland.
Exterior detail

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (172 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is ￥19,894
￥40,032 total
includes taxes & fees
Mar 30 - Mar 31
Glorious getaway on Portland's Eastern Promenade.
Microwave, oven, stovetop, dishwasher

Toast to 2026! Free Champagne for all Jan / Feb Bookings

Toast to 2026! Free Champagne for all Jan / Feb Bookings
South Portland
10.0 out of 10, Exceptional, (4 reviews)
"The house was very nice and had great accommodations for our group. The kitchen and living room was very accommodating for meals and hangouts and we were close to all of the activities we were looking to do"
United States
Justin R.
The price is ￥68,132
￥99,776 total
includes taxes & fees
Apr 5 - Apr 6
Toast to 2026! Free Champagne for all Jan / Feb Bookings
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top North Windham Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Clean spacious rooms, comfy beds good service"
Shreya 1-night trip
Posted 5 hours ago
Portland Regency Hotel & Spa

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?

The Globe House on Munjoy Hill - Walk to Breweries: This vacation home near North Windham is located in the city center and has a garden, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Basin and Sebago Lake 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.