A sunset over a lake surrounded by dense forests and a distant shoreline.

Long Island Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Long Island holiday rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (118 reviews)
"Really nice room and location"
United States
Victoria
The price is S$631
includes taxes & fees
22 Sept - 23 Sept
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is S$884
includes taxes & fees
15 Sept - 16 Sept
Evalina Hotel
A courtyard with a hammock, outdoor seating, and a view of boats on the water.

3. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is S$778
includes taxes & fees
24 Sept - 25 Sept
'osprey Cottage' South Freeport Home on Casco Bay!
A modern living room with a large sofa set, a coffee table, and a view of the ocean through large windows.

4. Oceanfront Home - Beach Access - Deck + Ping Pong

Oceanfront Home - Beach Access - Deck + Ping Pong
3.5 star property
Old Orchard Beach
The price is S$3,400
includes taxes & fees
16 Sept - 17 Sept
Oceanfront Home - Beach Access - Deck + Ping Pong
A living room with a gray sofa, a wooden coffee table, a ceiling fan, and a standing heater.

5. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is S$427
includes taxes & fees
20 Sept - 21 Sept
1/2 Mi to Pier: Wfh-friendly Apt in Maine!

6. 'beachfront 14' Condo on Old Orchard Beach

'beachfront 14' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
'beachfront 14' Condo on Old Orchard Beach

7. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is S$359
includes taxes & fees
27 Sept - 28 Sept
'beachfront 9' Condo on Old Orchard Beach
A spacious living room with large windows, a sofa, a chair, and a small table.

8. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is S$344
includes taxes & fees
23 Sept - 24 Sept
1 Mi to Maine Street! Mcm-style Home in Brunswick
A two-story house with a covered patio area featuring a table and chairs, a blue umbrella, and a 'Tenant Parking' sign.

9. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is S$411
includes taxes & fees
20 Sept - 21 Sept
Walk to Pier & Ocean: Apt in Old Orchard Beach!
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 Long Island Hotel Reviews

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

8/10 Good
"Bedding was clean, soft and warm. Room had a working tv, coffee maker and microwave. Complimentary breakfast was warm and delicious. Parking area was clean. Air conditioner worked but was loud. Bathroom door squeaked and room carpet along with stairway carpet really needed replacement or a really good shampoo. Room rate was good for my stay."
Elizabeth 2-night trip
Posted 1 hour ago
Quality Inn & Suites South Portland

Frequently asked questions

Are there holiday rentals in Long Island?

Yes, there are holiday rentals close to the most popular sights in Long Island, or you can select a more secluded option if you're looking for a relaxing stay. Long Island is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

How many holiday rentals are there in Long Island?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Long Island stay.

What’s there to see and do in Long Island?

While exploring the area, visit family-friendly sights like Maine Narrow Gauge Railroad, or get outside and enjoy nature at Sand Beach. In the wider area, you’ll find East End Beach and Willard Beach.

What’s a holiday rental in Long Island like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Long Island. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.