Long Island Holiday Homes from £144: Search Holiday Homes in Long Island

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 compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

1. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

11 Oct - 12 Oct

A window with a view of a snowy landscape and bare trees.

2. Tranquility between the Lakes & Sea

Westbrook

includes taxes & fees

14 Oct - 15 Oct

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 ♦ Perfect Location

West End

Susan d.

includes taxes & fees

29 Oct - 30 Oct

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

West Point

Rebecca

includes taxes & fees

1 Nov - 2 Nov

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

5. Captains Watch: A Coastal Escape

West Point

includes taxes & fees

6 Oct - 7 Oct

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

6. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

14 Oct - 15 Oct

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

7. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

includes taxes & fees

29 Oct - 30 Oct

A spacious living room with large windows, a sofa, a chair, and a small table.

8. 1 Mi to Maine Street! MCM-Style Home in Brunswick

Brunswick

Kendra G.

includes taxes & fees

20 Oct - 21 Oct

A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

9. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

includes taxes & fees

1 Nov - 2 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.

10. 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

29 Oct - 30 Oct

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.

11. 2 bedroom w/ expansive water views

West Point

Gregory M.

includes taxes & fees

1 Nov - 2 Nov

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

12. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

includes taxes & fees

13 Oct - 14 Oct

A wooden deck with outdoor seating and string lights.

13. Full sized home

Harpswell

Angela M.

includes taxes & fees

7 Oct - 8 Oct

A lush garden with a hammock, a variety of flowers, and a lake in the background.

14. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

includes taxes & fees

3 Nov - 4 Nov

A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

North Deering

Peter H.

includes taxes & fees

18 Oct - 19 Oct

A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

16. Fantastic Waterfront Views

West Point

Vanessa W.

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

17. Gorgeous 3-bedroom house in charming Portland

North Deering

Bridget M.

includes taxes & fees

31 Oct - 1 Nov

A two-story house with a balcony, a covered patio, and a fenced yard.

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

Munjoy Hill

Richard D.

includes taxes & fees

6 Oct - 7 Oct

A lakeside property with a deck, picnic table, and barbecue grill.

19. Camp Forever cottage

Harpswell

Dennis H.

includes taxes & fees

6 Oct - 7 Oct

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

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

Scarborough

Stuart R.

includes taxes & fees

13 Oct - 14 Oct

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Top Long Island Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent

"Nice, newer, clean hotel. We would stay there again."

Portland Regency Hotel & Spa

8/10 Good

"Our room was lovely, but the bathroom needs updating. Everything was clean, but showed signs of age inconsistent with a hotel of this level. The location is excellent- walkable and safe. The hotel site indicates “valet parking is available” but should read “required.” We were surprised by the situation. If I returned to Portland, I would stay here again."