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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 NZ$675
includes taxes & fees
19 Oct - 20 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

2. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
Fully Updated Airy Historic Home in South Freeport

3. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$709
includes taxes & fees
27 Sept - 28 Sept
Quiet Spot in lovely Freeport neighborhood

4. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is NZ$1,062
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home

5. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$569
includes taxes & fees
29 Sept - 30 Sept
Tranquility between the Lakes & Sea

6. 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$902
includes taxes & fees
27 Sept - 28 Sept
Modern & Sunny House Steps from the Promenade.

7. 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, (16 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is NZ$1,096
includes taxes & fees
1 Oct - 2 Oct
Rare West End Home • Walk to Old Port, Harbor View

8. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (12 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
Orchid Harbor, Bailey Island 3BR

9. 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$1,963
includes taxes & fees
28 Sept - 29 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (70 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

11. 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

12. 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, (20 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.

13. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 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 NZ$353
includes taxes & fees
29 Sept - 30 Sept
Mid Coast Getaway w/ water views

14. 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, (4 reviews)
"Clean, pet friendly, amazing location, great for large groups and very responsive host! Gave great recommendations"
United States
Erica G.
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

15. 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 NZ$1,266
includes taxes & fees
25 Oct - 26 Oct
The 87th Townhome - Local Landmark

16. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is NZ$1,207
includes taxes & fees
1 Oct - 2 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

17. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is NZ$635
includes taxes & fees
6 Oct - 7 Oct
Camp Forever cottage

18. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is NZ$1,097
includes taxes & fees
28 Sept - 29 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

19. 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 NZ$1,775
includes taxes & fees
28 Sept - 29 Sept
Luxe 5 Bed/ 3 Bath with Game Room & AC

20. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
9.0 out of 10, Wonderful, (2 reviews)
"The location was very convenient. Easy drive to downtown Saco and Biddeford. As well as very quick access to the highway so Portland and other points are easy to get to. Ample parking."
United States
Ellen L.
The price is NZ$917
includes taxes & fees
27 Oct - 28 Oct
Huge New Townhome 10mins from the 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

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Long Island Holiday Homes information

Number of reviews
442
Accommodation
699 Holiday Homes
Lowest Price
NZ$353
Highest Price
NZ$1,963