Long Island Holiday Houses

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

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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

Freeport

includes taxes & fees

11 Nov - 12 Nov

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

2. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

West End

Susan d.

includes taxes & fees

11 Nov - 12 Nov

A living room with a sofa, armchair, wooden coffee table, and a potted plant.

3. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

includes taxes & fees

11 Nov - 12 Nov

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

4. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

5. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Munjoy Hill

"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...

Maris P.

includes taxes & fees

11 Nov - 12 Nov

A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

6. Mid Coast Getaway w/ water views

West Point

Rebecca

includes taxes & fees

12 Nov - 13 Nov

A building named Willard Square with a storefront and a red vehicle parked outside.

7. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

A covered porch with a view of a lake and trees.

8. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

9. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

includes taxes & fees

16 Nov - 17 Nov

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.

Munjoy Hill

stacey p.

includes taxes & fees

11 Nov - 12 Nov

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

Harpswell

Ashma B.

includes taxes & fees

30 Nov - 1 Dec

A wooden deck with outdoor seating and string lights.

12. Full sized home

Harpswell

Erika T.

includes taxes & fees

7 Dec - 8 Dec

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

Windham

Michael S.

includes taxes & fees

16 Nov - 17 Nov

A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

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

Scarborough

Stuart R.

includes taxes & fees

11 Nov - 12 Nov

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

15. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering

Mike G.

includes taxes & fees

12 Nov - 13 Nov

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.

16. 2 bedroom w/ expansive water views

West Point

Gregory M.

includes taxes & fees

17 Nov - 18 Nov

A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

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

Munjoy Hill

Matt H.

includes taxes & fees

10 Dec - 11 Dec

A deck with white railings overlooking a body of water, boats, and a forested shoreline.

18. Captains Watch: A Coastal Escape

West Point

Holly G.

includes taxes & fees

15 Nov - 16 Nov

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

Freeport

Vanessa K.

includes taxes & fees

19 Nov - 20 Nov

A wooden covered porch with a green door, potted plants, and a red watering can.

20. Charming West End Victorian

Parkside

includes taxes & fees

7 Dec - 8 Dec

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Top Long Island Hotel Reviews

Clarion Pointe South Portland

10/10 Excellent

"The night desk lady was so friendly and helpfull. We will be staying at this location everytime I come to S Portlsnd for fun or medical reasons. Its like seeing a friend we never knew we had. She is extremely helpfull n accommodating. Best employee at any hotels we've stayed at n we've stayed at A LOT OF HOTELS FROM MAINE TO VA YEARLY..."

Portland Harbor Hotel

10/10 Excellent

"There is a $35 per day amenities charge to your room. You can use it for drinks, food at the hotel. But if you don't use it, they still charge you. It's a great hotel, great location. That charge was a surprise to me. They did tell me about it when I was checking in, but I don't remember seeing it while searching for the hotel. But I did love my stay. I'd stay there again."

Clarion Hotel Portland Airport ME

10/10 Excellent

"The room was spacious but either too hot or two cold. The heat did not oscillate/cycle with much sensitivity. The bedding should be changed (dated) although it was clean. No heat in bathroom. However, it was very pleasant and staff were friendly. Dining room was clean and coffee was excellent. Guests around me loved their breakfast dish. I went to Becky’s as a personal favorite for mornings in Portland."

Find out more about Long Island

Long Island Holiday Homes information

Number of reviews	385
Accommodation	692 Holiday Homes
Lowest Price	NZ$361
Highest Price	NZ$2,749

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Long Island holiday homes

1. Quiet Spot in lovely Freeport neighborhood

2. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port