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Holiday Homes in Long Island

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Our top choices for Long Island holiday homes

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 and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AU$513
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

2. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$783
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.

3. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is AU$427
includes taxes & fees
22 Sept - 23 Sept
Serenity between the lakes and seashore

4. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 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 AU$818
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home

5. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is AU$558
includes taxes & fees
21 Sept - 22 Sept
Quiet Spot in lovely Freeport desert pines neighborhood

6. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is AU$764
includes taxes & fees
18 Sept - 19 Sept
Fully Updated Airy Historic Home in South Freeport

7. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AU$927
includes taxes & fees
22 Sept - 23 Sept
The Globe House on Munjoy Hill - Walk to Breweries

8. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AU$514
includes taxes & fees
22 Sept - 23 Sept
Full sized home

9. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AU$476
includes taxes & fees
13 Oct - 14 Oct
Tranquility between the Lakes & Sea

10. 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 price is AU$1,036
includes taxes & fees
20 Sept - 21 Sept
The 87th Townhome - Local Landmark

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is AU$1,109
includes taxes & fees
28 Sept - 29 Sept
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

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

Rare West End Home • Walk to Old Port, Harbor View
West End
9.8 out of 10, Exceptional, (14 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is AU$909
includes taxes & fees
24 Sept - 25 Sept
Rare West End Home • Walk to Old Port, Harbor View

13. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (3 reviews)
"The property was beautifully decorated, cleaned to perfection, and a great size home for our family trip. Thank you Mike and Kate!"
United States
Gina H.
The price is AU$1,370
includes taxes & fees
21 Sept - 22 Sept
Luxe 5 Bed/ 3 Bath with Game Room & AC

14. 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, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is AU$1,798
includes taxes & fees
22 Sept - 23 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

15. 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, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is AU$387
includes taxes & fees
23 Sept - 24 Sept
1 Mi to Maine Street! MCM-Style Home in Brunswick

16. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (9 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is AU$347
includes taxes & fees
20 Sept - 21 Sept
Mid Coast Getaway w/ water views

17. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Oakdale
10.0 out of 10, Exceptional, (1 review)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
United States
Andy W.
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

18. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (67 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$509
includes taxes & fees
23 Sept - 24 Sept
Camp Forever cottage

19. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 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 AU$471
includes taxes & fees
17 Oct - 18 Oct
2 bedroom w/ expansive water views

20. SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is AU$1,369
includes taxes & fees
24 Sept - 25 Sept
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
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

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Long Island Holiday Homes information

Number of reviews
512
Accommodation
699 Holiday Homes
Lowest Price
AU$347
Highest Price
AU$1,798

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