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Littlejohn Island Holiday Rentals

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Our top choices for Littlejohn Island holiday rentals

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (122 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$801
includes taxes & fees
25 Oct - 26 Oct
The Weldon Hotel

2. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (113 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is NZ$821
includes taxes & fees
13 Oct - 14 Oct
Ocean View East End Studio in a Historic Victorian

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (13 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,206
includes taxes & fees
27 Oct - 28 Oct
Evalina Hotel

4. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (185 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is NZ$820
includes taxes & fees
1 Oct - 2 Oct
Glorious getaway on Portland's Eastern Promenade.

5. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is NZ$500
includes taxes & fees
26 Oct - 27 Oct
Adorable Portland getaway on the Eastern Promenade

6. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is NZ$519
includes taxes & fees
30 Sept - 1 Oct
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

7. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is NZ$2,129
includes taxes & fees
6 Oct - 7 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

8. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$964
includes taxes & fees
26 Oct - 27 Oct
Modern & Sunny House Steps from the Promenade.

9. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is NZ$861
includes taxes & fees
26 Oct - 27 Oct
Arlie`s Digs! - One Block To Willard Beach!

10. 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 NZ$635
includes taxes & fees
4 Oct - 5 Oct
Glamping cabin w/ full bath + spa access - 21

11. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is NZ$1,070
includes taxes & fees
30 Sept - 1 Oct
Lush Coastal Downtown Home - Beaches & Shopping

12. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
The price is NZ$1,947
includes taxes & fees
7 Oct - 8 Oct
Three bedroom in United States of America, Freeport

13. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is NZ$640
includes taxes & fees
5 Oct - 6 Oct
Full sized home

14. 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 NZ$635
includes taxes & fees
4 Oct - 5 Oct
Modern cabin w/ full bath & kitchenette - 03

15. Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful apartment. Great location. Very comfortable and all amenities needed."
United States
Navina F.
The price is NZ$1,097
includes taxes & fees
27 Oct - 28 Oct
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

16. THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (5 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is NZ$858
includes taxes & fees
30 Sept - 1 Oct
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

17. Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is NZ$1,239
includes taxes & fees
4 Oct - 5 Oct
Portland’s Best Ocean Views from a 40-Foot Private Deck

18. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (61 reviews)
"Very clean and has a lot of amenities"
United States
Philip
The price is NZ$874
includes taxes & fees
30 Sept - 1 Oct
Spacious 3 BR in Portland's Libbytown!

19. 2 Bedroom Apartment on Top Floor in Portland's West End

2 Bedroom Apartment on Top Floor in Portland's West End
West End
10.0 out of 10, Exceptional, (88 reviews)
"The rooftop deck makes the climb worth it. Everything was clean neat and organized. Great beds. Communication was fast and friendly. Thanks for a great stay. "
United States
TODD H.
The price is NZ$853
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom Apartment on Top Floor in Portland's West End

20. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is NZ$702
includes taxes & fees
30 Oct - 31 Oct
Peaceful & minutes from the Old Port with private parking
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 Littlejohn Island Hotel Reviews

Find out more about Littlejohn Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Littlejohn Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Littlejohn Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Littlejohn Island. Seeing all the best attractions is bound to make you fall in love with Littlejohn Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Littlejohn Island short-term rentals, that won’t be hard to do.

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