Little Falls-South Windham Holiday Rentals

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Our top choices for Little Falls-South Windham holiday rentals

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is NZ$644
includes taxes & fees
25 Dec - 26 Dec
The Weldon Hotel
9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is NZ$371
includes taxes & fees
22 Dec - 23 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland
9.8 out of 10, Exceptional, (227)
"The view off the deck was breathtaking "
United States
Raymond
The price is NZ$582
includes taxes & fees
17 Dec - 18 Dec
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
The price is NZ$2,142
includes taxes & fees
11 Jan - 12 Jan 2026
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
9.6 out of 10, Exceptional, (67)
"Great location, clean and the perfect beach front property!! "
United States
Alanna M.
The price is NZ$2,354
includes taxes & fees
12 Jan - 13 Jan 2026
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
9.8 out of 10, Exceptional, (197)
"My family had a wonderful time! The house was perfect for us. It was comfy and so well equipped.The location was absolutely perfect. The neighborhood was quiet and friendly. "
United States
Maryann A.
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Apartment in Deering Center

Private Entrance Residential Portland
9.2 out of 10, Wonderful, (5)
"Check in was simple. Quaint place. "
United States
Danielle C.
Private Entrance Residential Portland

Apartment in West Bayside

Studio Unit Walkable Everywhere
5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is NZ$241
includes taxes & fees
17 Dec - 18 Dec
Studio Unit Walkable Everywhere
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
9.8 out of 10, Exceptional, (65)
"Nice spot to stay with our pup! Chris was available and helpful, and it’s clear he takes care of his property. "
United States
John and Lori W.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
9.8 out of 10, Exceptional, (7)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
THE LILLIPAD.Off-grid A frame. Sebago lake region!

Cottage in Long Island

Updated Long Island Maine Cottage
10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
9.8 out of 10, Exceptional, (36)
"Great spot...everything was great "
United States
Frank R.
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Holiday Home in Portland

Back yard paradise
9.8 out of 10, Exceptional, (22)
"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "
United States
Justin J.
Back yard paradise
9.0 out of 10, Wonderful, (2)
"We really enjoyed our stay. The house had room for everybody and most of the things we needed. The location was great near the beach and boardwalk. Great time"
United States
MIchelle G.
Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub
9.8 out of 10, Exceptional, (122)
"The house was clean and homey…everything was well stocked and supplies were even there for our pet…great access to the highway…the views were beautiful…would definitely recommend! "
United States
Michelle M.
The price is NZ$441
includes taxes & fees
21 Dec - 22 Dec
City Amenities, Casco Bay Sunrises and Natural Beauty
9.4 out of 10, Exceptional, (128)
"This is a great place. A few minor hiccups which were taken care quickly . You can’t beat the views"
United States
Kimberly A.
Gorgeous ocean-front home with stunning beach views
8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
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

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, 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 NZ$241 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?

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!: This holiday home rental outside of Little Falls-South Windham is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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

While exploring the area, visit family-friendly sights like Seacoast Adventure, 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.