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Holiday Rentals in Long Island

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Our top choices for Long Island holiday rentals

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (128 reviews)
"Really nice room and location"
United States
Victoria
The price is €245
includes taxes & fees
18 Nov - 19 Nov
The Weldon Hotel

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (16 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is €402
includes taxes & fees
30 Nov - 1 Dec
Evalina Hotel

3. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is €211
includes taxes & fees
31 Oct - 1 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

4. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (73 reviews)
"Great stay!"
United States
Jason M.
The price is €461
includes taxes & fees
18 Nov - 19 Nov
Arlie`s Digs! - One Block To Willard Beach!

5. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (137 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty

6. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (63 reviews)
"The apartment is very comfortable with everything we needed We loved the quiet neighborhood and the location was really great within walking distance to both the beach area and downtown shops & restaurants."
United States
maureen
The price is €425
includes taxes & fees
22 Nov - 23 Nov
Vintage Maine & Modern Convenience in Portlands Exclusive East End

7. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (63 reviews)
"Nice host, great location & property."
United States
Brittney C.
The price is €448
includes taxes & fees
31 Oct - 1 Nov
Spacious 3 BR in Portland's Libbytown!

8. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (11 reviews)
"Great spot. Roomy. Close to shops and ferries. It had everything we needed to see Portland."
United States
Benton M.
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

9. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Clean and comfortable stay in great location! "
United States
Juliet S.
The price is €721
includes taxes & fees
31 Oct - 1 Nov
Prime Old Port 3BR • Free Parking • Sleeps 8

10. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.2 out of 10, Wonderful, (5 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
The price is €82
includes taxes & fees
1 Nov - 2 Nov
Great suburban location close to town!

11. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (17 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is €75
includes taxes & fees
1 Nov - 2 Nov
Portland 1-bedroom with enclosed porch & parking

12. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (47 reviews)
"Very comfortable and stocked well. Lacked for nothing and able to walk to most places. Host checked in which was very nice. Enjoyed Portland."
United States
sheila g.
East end. Walk to food, beer and downtown fun.

13. Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.6 out of 10, Exceptional, (24 reviews)
"Super cute apartment that was perfect for our stay in Portland. It was close to Old Port that had lots of cute shops and restaurants."
United States
Erin
The price is €310
includes taxes & fees
2 Nov - 3 Nov
Luxury Condo Downtown Portland Old Port

14. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is €137
includes taxes & fees
2 Nov - 3 Nov
Bright & Spacious Apartment with Amazing Shower

15. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic little spot. Great location and easy to find parking even if not using what is reserve. Home had everything necessary for a stay. Hosts were prompt with communication."
United States
Susan
NEW 1 BDR-Heart of Munjoy Hill

16. Three Gables Back Cove by Everrow

Three Gables Back Cove by Everrow
Rosemont
10.0 out of 10, Exceptional, (15 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is €439
includes taxes & fees
3 Nov - 4 Nov
Three Gables Back Cove by Everrow

17. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (34 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is €137
includes taxes & fees
5 Nov - 6 Nov
Beautiful 1st Floor Apartment & Amazing Shower

18. West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
9.8 out of 10, Exceptional, (30 reviews)
"The space was pristine, comfortable, homey with an excellent location situated to shops and restaurants. Jennifer was a welcoming and warm host and we had no issues at all during our stay!"
United States
Luke E.
The price is €289
includes taxes & fees
2 Nov - 3 Nov
West End Bright Spot with Parking.

19. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (6 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
East End Guesthouse

20. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (108 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is €247
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
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

Find out more about Long Island

Everything you need to know about Long Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Long Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Long Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Long Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Long Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Long Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Long Island holiday rentals we have selected for you start as low as €119 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Long Island rentals

At Expedia, we put the best Long Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Long Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Long Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Long Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Long Island?

Yes, there are holiday rentals close to the most popular sights in Long Island, or you can select a more secluded option if you're looking for a relaxing stay. Long Island is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best holiday rentals that Long Island has to offer?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Long Island is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Long Island?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Long Island stay.

What’s there to see and do in Long Island?

While exploring the area, visit family-friendly sights like Maine Narrow Gauge Railroad, or get outside and enjoy nature at Sand Beach. In the wider area, you’ll find East End Beach and Willard Beach.

What’s a holiday rental in Long Island like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Long Island. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.