Vacation rentals in Long Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Long Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.
8–15 May
$245 NZD per night
4.97 out of 5 average rating, 101 reviews
Guest favourite
Guesthouse in Portland
Beautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.
28 Apr – 5 May
$273 NZD per night
4.95 out of 5 average rating, 277 reviews
Guest favourite
Apartment in Portland
RETRO BnB in the Heart of East End Portland
Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!
4–11 May
$288 NZD per night
4.97 out of 5 average rating, 372 reviews

Popular amenities for Long Island holiday rentals

Stay near Long Island's top sights

Peaks Island176 locals recommend
Battery Steele4 locals recommend
Diamond's Edge Restaurant and Marina13 locals recommend
Fifth Maine Regiment Museum6 locals recommend
Crown Jewel7 locals recommend
Byers & Sons Long Island Bakehouse3 locals recommend

Other great holiday rentals in Long Island

Guest favourite
Guest suite in Freeport
Solar Suite surrounded by Nature
15–22 Jul
$229 NZD per night
4.96 out of 5 average rating, 114 reviews
Guest favourite
Guest suite in Portland
Garden Suite @ A Peaceful Oasis on Munjoy Hill
6–13 Jan
$203 NZD per night
4.9 out of 5 average rating, 337 reviews
Guest favourite
Apartment in Portland
Munjoy Hill, East End 1 BR Portland, ME
31 Mar – 7 Apr
$216 NZD per night
4.97 out of 5 average rating, 351 reviews
Guest favourite
Apartment in Portland
No cleaning fee! Location, location!
17–24 Jan
$175 NZD per night
4.94 out of 5 average rating, 449 reviews
Guest favourite
Guest suite in Windham
Millers Private Studio on Highland Lake
3–10 Nov
$219 NZD per night
4.93 out of 5 average rating, 149 reviews
Guest favourite
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
22–29 Jan
$130 NZD per night
4.94 out of 5 average rating, 326 reviews
Guest favourite
Guesthouse in Windham
Cottage on Black Brook Preserve
9–16 Apr
$239 NZD per night
5.0 out of 5 average rating, 213 reviews
Superhost
Apartment in Portland
Spacious and Comfortable Private Apartment
31 Oct – 7 Nov
$157 NZD per night
4.82 out of 5 average rating, 347 reviews
Guest favourite
Apartment in Portland
Hip & Cozy, high end Modern Design
13–20 Nov
$271 NZD per night
4.9 out of 5 average rating, 341 reviews
Guest favourite
Guest suite in Portland
Sunny West End Guest Suite with Harbor Views
24–29 Mar
$321 NZD per night
4.99 out of 5 average rating, 264 reviews
Guest favourite
Apartment in South Portland
Sunny and beautiful brick house apartment
18–25 Oct
$330 NZD per night
4.91 out of 5 average rating, 148 reviews
Guest favourite
Apartment in Gorham
Cozy Private 1 Bedroom Apartment - Gorham Village
7–14 Sep
$214 NZD per night
4.96 out of 5 average rating, 194 reviews

Quick stats about holiday rentals in Long Island

Total rentals

60 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

2K reviews

Nightly prices starting at

$131 NZD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Long Island