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

Holiday Homes in Long Island

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Long Island holiday homes

Interior

1. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place. Good location."
United States
Rob M.
The price is €367
includes taxes & fees
3 Sept - 4 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Exterior

2. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is €513
includes taxes & fees
23 Aug - 24 Aug
Willard Square Family Home
Outdoor dining

3. Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is €499
includes taxes & fees
1 Sept - 2 Sept
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

4. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (61 reviews)
"Wonderful stay!"
United States
Erika T.
The price is €321
includes taxes & fees
24 Aug - 25 Aug
Full sized home
Interior

5. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is €362
includes taxes & fees
8 Sept - 9 Sept
Tranquility between the Lakes & Sea
TV, fireplace, books

6. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (11 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
1 Mi to Maine Street! MCM-Style Home in Brunswick
TV, offices

7. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is €549
includes taxes & fees
16 Aug - 17 Aug
Fully Updated Airy Historic Home in South Freeport
Interior

8. Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage

Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
Cape Elizabeth
10.0 out of 10, Exceptional, (6 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is €754
includes taxes & fees
24 Aug - 25 Aug
Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
TV

9. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is €267
includes taxes & fees
28 Aug - 29 Aug
Mid Coast Getaway w/ water views
Interior

10. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (17 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
Spacious 4-bedroom house located in the heart of Portland, ME.
Terrace/patio

11. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (62 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is €315
includes taxes & fees
25 Aug - 26 Aug
Camp Forever cottage
Exterior detail

12. 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, (78 reviews)
"Everything was very well stocked!"
United States
Sally O.
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
TV, fireplace

13. Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View
West End
10.0 out of 10, Exceptional, (12 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is €670
includes taxes & fees
19 Aug - 20 Aug
Rare West End Home • Walk to Old Port, Harbor View
Outdoor dining

14. Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.6 out of 10, Excellent, (4 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
Spacious Portland Home + Parking
TV, offices

15. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is €679
includes taxes & fees
19 Aug - 20 Aug
Windham Lakefront: Fire Pit and Modern Comforts
Exterior

16. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.4 out of 10, Exceptional, (9 reviews)
"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"
United States
Amy B.
The 87th Townhome - Local Landmark
Beach nearby

17. Beachwood Cottage by Bayley Vacation Rentals

Beachwood Cottage by Bayley Vacation Rentals
Grand Beach
9.8 out of 10, Exceptional, (15 reviews)
"Great place Location was excellent and there are many activities nearby. The beach was just across the street! "
United States
Douglas K.
The price is €1,024
includes taxes & fees
25 Aug - 26 Aug
Beachwood Cottage by Bayley Vacation Rentals
Property grounds

18. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is €1,595
includes taxes & fees
8 Sept - 9 Sept
Classic New England Waterfront House Big Lawn Beautiful Sunrise
Interior

19. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (6 reviews)
The price is €889
includes taxes & fees
1 Sept - 2 Sept
Three bedroom in United States of America, Freeport
TV

20. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (4 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is €360
includes taxes & fees
7 Sept - 8 Sept
2 bedroom w/ expansive water views
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

8/10 Good
"Everything was in close walking distance, and the shuttle was very useful."
Deveda 3-night trip
Posted 1 hour ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Long Island

Long Island Holiday Homes information

Number of reviews
401
Accommodation
708 Holiday Homes
Lowest Price
€267
Highest Price
€1,595