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

Holiday Homes in Long Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Long Island holiday homes

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

1. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €311
includes taxes & fees
12 Nov - 13 Nov
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

2. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is €411
includes taxes & fees
12 Nov - 13 Nov
Fully Updated Airy Historic Home in South Freeport
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

3. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is €301
includes taxes & fees
16 Nov - 17 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

4. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 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 €188
includes taxes & fees
12 Nov - 13 Nov
Mid Coast Getaway w/ water views
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

5. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is €365
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is €387
includes taxes & fees
23 Nov - 24 Nov
Mere Point Sunrise Views at Eastern Shore!
A building named Willard Square with a storefront and a red vehicle parked outside.

7. 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.
Willard Square Family Home
A covered porch with a view of a lake and trees.

8. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is €620
includes taxes & fees
8 Dec - 9 Dec
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is €684
includes taxes & fees
22 Nov - 23 Nov
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A modern kitchen with a central island, a dining area with a sofa and chairs, and a living room with a colorful rug and plants.

10. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is €472
includes taxes & fees
12 Nov - 13 Nov
Modern & Sunny East End House.
A lush garden with a hammock, a variety of flowers, and a lake in the background.

11. 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 €1,374
includes taxes & fees
30 Nov - 1 Dec
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A wooden deck with outdoor seating and string lights.

12. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Great house! Enjoyed our stay very much. Comfortable, clean, and many nice extra touches i.e. games, books."
United States
Jill J.
The price is €301
includes taxes & fees
30 Nov - 1 Dec
Full sized home
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

13. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
Heated Game Room, Coastal Maine Cape Sleeps 10
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

14. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 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 €204
includes taxes & fees
17 Nov - 18 Nov
2 bedroom w/ expansive water views
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

15. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
8.8 out of 10, Excellent, (3 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
The price is €245
includes taxes & fees
15 Nov - 16 Nov
Captains Watch: A Coastal Escape
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

16. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is €909
includes taxes & fees
16 Nov - 17 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A wooden covered porch with a green door, potted plants, and a red watering can.

17. Charming West End Victorian

Charming West End Victorian
Parkside
The price is €618
includes taxes & fees
1 Dec - 2 Dec
Charming West End Victorian
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

18. 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, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is €777
includes taxes & fees
12 Nov - 13 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.
A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

19. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"The house was amazing. We would recommend this property to anyone. The view, stars at night and accessibility to where we wanted to visit, was perfect."
United States
Vanessa K.
The price is €783
includes taxes & fees
18 Nov - 19 Nov
Casco Bay Oceanfront Retreat by Everrow
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

20. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (23 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €248
includes taxes & fees
12 Nov - 13 Nov
Fantastic Waterfront 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Long Island Hotel Reviews

The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Nice property. High parking fees"
SCOTT 1-night trip
Posted less than an hour ago
The Westin Portland Harborview

Find out more about Long Island

Long Island Holiday Homes information

Number of reviews
398
Accommodation
703 Holiday Homes
Lowest Price
€188
Highest Price
€1,374