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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Little Falls-South Windham holiday rentals

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

1. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
The price is £52
includes taxes & fees
16 Nov - 17 Nov
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.

2. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (19 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is £54
includes taxes & fees
15 Nov - 16 Nov
Portland 1-bedroom with enclosed porch & parking
A gym with treadmills, elliptical machines, and exercise balls.

3. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.4 out of 10, Exceptional, (23 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is £91
includes taxes & fees
14 Nov - 15 Nov
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

4. 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, (16 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 £284
includes taxes & fees
16 Nov - 17 Nov
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A covered porch with a view of a lake and trees.

5. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is £494
includes taxes & fees
18 Nov - 19 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A bedroom with a wooden floor, a bed with a patterned bedspread, a nightstand, a chair, and a desk with a lamp.

6. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (27 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
The price is £93
includes taxes & fees
19 Nov - 20 Nov
Studio Apartment near downtown Walkable!
A room with a leather armchair, ottoman, wooden cabinet with decorative items, and a television mounted on the wall.

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

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
10.0 out of 10, Exceptional, (4 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
The price is £219
includes taxes & fees
30 Nov - 1 Dec
Cozy 1-bedroom cottage in soothing Standish with AC
A brick wall with a logo and the text 'THE SEND BREWING CO.'

8. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is £150
includes taxes & fees
15 Nov - 16 Nov
Sunny Spot with Private Parking
A living room with a sofa, armchairs, a coffee table, and a potted plant.

9. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is £97
includes taxes & fees
15 Nov - 16 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

10. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 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 £104
includes taxes & fees
17 Nov - 18 Nov
Bright & Spacious Apartment with Amazing Shower
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

11. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
The price is £202
includes taxes & fees
20 Nov - 21 Nov
The Weldon Hotel
A two-story house with a covered front porch and a brick foundation.

12. Three Gables Back Cove by Everrow

Three Gables Back Cove by Everrow
Rosemont
10.0 out of 10, Exceptional, (15 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is £353
includes taxes & fees
16 Nov - 17 Nov
Three Gables Back Cove by Everrow
A multi-story building with a stone facade, large windows, and a corner entrance.

13. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is £301
includes taxes & fees
13 Dec - 14 Dec
Evalina Hotel
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

14. 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 £208
includes taxes & fees
15 Nov - 16 Nov
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A brick wall with a logo and the text 'THE SEND BREWING CO.'

15. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (14 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is £177
includes taxes & fees
15 Nov - 16 Nov
Peaceful & minutes from Old Port w/private parking
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

16. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!"
United States
Ryan B.
The price is £167
includes taxes & fees
17 Nov - 18 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

17. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is £253
includes taxes & fees
16 Nov - 17 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

18. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (97 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is £253
includes taxes & fees
15 Nov - 16 Nov
Walk to Old Port ♦ West End Condo ♦ Parking
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

19. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is £571
includes taxes & fees
30 Nov - 1 Dec
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

20. 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 £201
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake
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 Little Falls-South Windham Hotel Reviews

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

Homewood Suites by Hilton Portland

Homewood Suites by Hilton Portland
Scarborough

10/10 Excellent

Great location. Tasty pub next door. Great room.
United Kingdom
Edward
Reviewed June 28, 2025
Homewood Suites by Hilton Portland

Find out more about Little Falls-South Windham

Everything you need to know about Little Falls-South Windham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Little Falls-South Windham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Little Falls-South Windham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Little Falls-South Windham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Little Falls-South 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 Little Falls-South Windham holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Little Falls-South Windham holiday rentals we have selected for you start as low as £51 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Little Falls-South Windham rentals

At Expedia, we put the best Little Falls-South Windham holiday 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 Little Falls-South 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 Little Falls-South Windham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Little Falls-South 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 a holiday rental in Little Falls-South Windham?

Yes, there are holiday rentals close to the most popular sights in Little Falls-South Windham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Little Falls-South Windham has to offer?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Little Falls-South Windham is located on the beach, and has a fireplace, a balcony 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Little Falls-South Windham?

While exploring the area, visit family-friendly sights like Maine Narrow Gauge Railroad, or get outside and enjoy nature at Thompson's Point. In the wider area, you’ll find St Josephs College and University of New England.

What are holiday rentals like in Little Falls-South Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Little Falls-South Windham. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.