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Long Island Holiday Rentals

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Our top choices for Long Island holiday rentals

1. Entire House & Windmill Coast Retreat

Entire House & Windmill Coast Retreat
Glace Bay
10.0 out of 10, Exceptional, (2 reviews)
"Fabulous stay! Clean, efficient and friendly hosts!"
United States
Wanda H.
The price is NZ$436
includes taxes & fees
30 Aug - 31 Aug
Entire House & Windmill Coast Retreat

2. Sky-View | Modern 2BR Retreat + Balcony (490861)

Sky-View | Modern 2BR Retreat + Balcony (490861)
Sydney
10.0 out of 10, Exceptional, (1 review)
"My family and I were thrilled to walk into such a beautiful very new apartment. There are so many details and special touches to make this place our home. Spacious bedrooms, a kitchen stocked with everything that you could possibly think of and a private, quiet deck. The living room is spacious with two comfortable couches so everyone can enjoy the largest smart television I’ve ever seen anywhere I’ve rented! Figgi & Dr. Eappen sent very clear instructions to check in with along with wifi...
Canada
Eiron
The price is NZ$529
includes taxes & fees
30 Aug - 31 Aug
Sky-View | Modern 2BR Retreat + Balcony (490861)

3. Garden Suite | Modern 2BR with Private Yard

Garden Suite | Modern 2BR with Private Yard
Sydney
10.0 out of 10, Exceptional, (1 review)
"My family loved our stay at Philip and Figgi’s place! It was spacious, clean, and great for our two nights in Sydney."
Canada
Cailin
The price is NZ$559
includes taxes & fees
1 Sept - 2 Sept
Garden Suite | Modern 2BR with Private Yard

4. Modern Sydney Retreat - Private 4BR, 2BR for Groups of 8

Modern Sydney Retreat - Private 4BR, 2BR for Groups of 8
Sydney
10.0 out of 10, Exceptional, (3 reviews)
"Loved this place! My family came together from out west, NS and Nfld to celebrate our mothers life and this was the perfect spot where our adult sons and daughters could hang out separately from us more senior adults.Loved everything from the kitchen, bathrooms, bedrooms to the incredible TVs in the wall!Thanks guys, we will be back!"
United States
Ron M.
The price is NZ$922
includes taxes & fees
30 Aug - 31 Aug
Modern Sydney Retreat - Private 4BR, 2BR for Groups of 8

5. Full house

Full house
Sydney
9.2 out of 10, Wonderful, (13 reviews)
"Excellent"
Canada
FNU
The price is NZ$707
includes taxes & fees
27 Aug - 28 Aug
Full house

6. Sydney Retreat | 3BR, 2 Bath Home with Deck & BBQ

Sydney Retreat | 3BR, 2 Bath Home with Deck & BBQ
Sydney
8.0 out of 10, Very good, (1 review)
"This property was set up very well with amenities and usable household items. My favorites were well functioning the air conditioning, sunny usable deck and cotton sheets. Some things need to be tended to, otger than that, excelkent."
United States
Tricia B.
The price is NZ$869
includes taxes & fees
1 Sept - 2 Sept
Sydney Retreat | 3BR, 2 Bath Home with Deck & BBQ

7. The new Berkshire House

The new Berkshire House
Sydney
8.8 out of 10, Excellent, (12 reviews)
"Had a great stay with the family. "
Canada
David
The price is NZ$647
includes taxes & fees
1 Sept - 2 Sept
The new Berkshire House

8. Rita’s Retreat Main House ~ Indoor Saltwater Pool ~ with Lake View!

Rita’s Retreat Main House ~ Indoor Saltwater Pool ~ with Lake View!
Sydney
7.6 out of 10, Good, (5 reviews)
":)"
Canada
Kristen P.
The price is NZ$1,048
includes taxes & fees
1 Sept - 2 Sept
Rita’s Retreat Main House ~ Indoor Saltwater Pool ~ with Lake View!

9. Rita's Retreat: The Bachelor ~ Indoor Saltwater Pool ~ with Lake View!

Rita's Retreat: The Bachelor ~ Indoor Saltwater Pool ~ with Lake View!
Sydney
8.8 out of 10, Excellent, (9 reviews)
"Did not know that there were so many stairs to get to and from the bachelor apt., However Hosts were there at the time we arrived to check on things and graciously helped us up the stairs with our bags ! We really appreciated their friendliness and kindness after a long day . The oatmeal cookies that were left for us as a special treat were fantastic and waking up to a beautiful view with Canada geese on the lawn by the lake was amazing!"
Canada
Naomi
The price is NZ$463
includes taxes & fees
2 Sept - 3 Sept
Rita's Retreat: The Bachelor ~ Indoor Saltwater Pool ~ with Lake View!

10. Ocean front Cranberry Cottage. Close-NFLD FERRY, Cabot Trail, Baddeck, Louisburg

Ocean front Cranberry Cottage. Close-NFLD FERRY, Cabot Trail, Baddeck, Louisburg
Sydney Mines
9.6 out of 10, Exceptional, (18 reviews)
"We were in Sydney Mines to visit a friend and Cranberry Cottage was just perfect! Incredible location - a front row seat to the start of lobster season. Well renovated and extremely well equipped. Would return in a heartbeat."
United States
Jan C.
The price is NZ$821
includes taxes & fees
14 Sept - 15 Sept
Ocean front Cranberry Cottage. Close-NFLD FERRY, Cabot Trail, Baddeck, Louisburg

11. Rita's Retreat: Rita Suite ~ Indoor Saltwater Pool ~ with Lake View!

Rita's Retreat: Rita Suite ~ Indoor Saltwater Pool ~ with Lake View!
Sydney
9.4 out of 10, Exceptional, (8 reviews)
"Very clean and spacious. Loved the pool."
Canada
Carol B.
The price is NZ$761
includes taxes & fees
1 Sept - 2 Sept
Rita's Retreat: Rita Suite ~ Indoor Saltwater Pool ~ with Lake View!

12. Apartment in North Sydney

Apartment in North Sydney
North Sydney
The price is NZ$374
includes taxes & fees
5 Sept - 6 Sept
Apartment in North Sydney

13. whole house at North Sydney

whole house at North Sydney
North Sydney
The price is NZ$676
includes taxes & fees
27 Aug - 28 Aug
whole house at North Sydney

14. Beach access with Ocean View; Cabot Trail 25 km away.

Beach access with Ocean View; Cabot Trail 25 km away.
Black Rock
9.0 out of 10, Wonderful, (11 reviews)
"This was the perfect place for my husband and I to celebrate our 3 year anniversary and explore Cape Breton. Great location and the private beach was extra special. "
Canada
Anonymous traveller
The price is NZ$397
includes taxes & fees
21 Aug - 22 Aug
Beach access with Ocean View; Cabot Trail 25 km away.

15. Eagles Nest Converted Shipping Container at Sally's Brook Wilderness Cabins

Eagles Nest Converted Shipping Container at Sally's Brook Wilderness Cabins
Englishtown
10.0 out of 10, Exceptional, (5 reviews)
"What a neat experience and fantastic place to unwind . Had a great time exploring the area and Cabot trail"
United States
Kris A.
The price is NZ$577
includes taxes & fees
1 Sept - 2 Sept
Eagles Nest Converted Shipping Container at Sally's Brook Wilderness Cabins

16. Hummingbird Hike-In Sleeping Pod at Sally's Brook Wilderness Cabins

Hummingbird Hike-In Sleeping Pod at Sally's Brook Wilderness Cabins
Englishtown
9.8 out of 10, Exceptional, (9 reviews)
"Will definitely be coming back and telling everyone I know to go I wish I stayed longer Lisa the manager was beyond helpful Absolutely beautiful place and perfect location "
Canada
Charlene R.
The price is NZ$296
includes taxes & fees
2 Sept - 3 Sept
Hummingbird Hike-In Sleeping Pod at Sally's Brook Wilderness Cabins

17. Raven's Roost Hike-in Sleeping Cabin at Sally's Brook Off-Grid Luxury Cabins

Raven's Roost Hike-in Sleeping Cabin at Sally's Brook Off-Grid Luxury Cabins
Englishtown
10.0 out of 10, Exceptional, (5 reviews)
"This was an amazing property. Well maintained. Clean and great facilities. Lisa was amazing and other staff were very friendly. We did the trail to the brook and it was nicely marked. Getting up the hill was a challenge with heavy bags so consider taking staff up on offered assistance. Will for sure recommend this to others if they are traveling in the area."
Canada
Giovanni
The price is NZ$418
includes taxes & fees
23 Aug - 24 Aug
Raven's Roost Hike-in Sleeping Cabin at Sally's Brook Off-Grid Luxury Cabins

18. The White Pine Cottage on the Cabot Trail

The White Pine Cottage on the Cabot Trail
Englishtown
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful environment, cute little cozy spot ! Host was very helpful ."
Canada
Caleb
The price is NZ$469
includes taxes & fees
19 Sept - 20 Sept
The White Pine Cottage on the Cabot Trail

19. Beaver Dome at Cabot Shores Wilderness Resort

Beaver Dome at Cabot Shores Wilderness Resort
Englishtown
6.0 out of 10, (1 review)
"The dome itself was lovely and well situated on the water. The bed was uncomfortable, but the linens were clean. I was very disappointed in the facilities. I have no issues with using a pit toilet, however you must provide some running water for guests. The only way I was able to fill up water bottles was to ask the people at the lodge to go into the kitchen to fill my water bottles. I was also incredibly disgusted by the showers at Cabot Shores. We were first directed to use the showers in the...
United States
Katherine B.
The price is NZ$354
includes taxes & fees
13 Sept - 14 Sept
Beaver Dome at Cabot Shores Wilderness Resort

20. Cabot Shores Wilderness Resort

Cabot Shores Wilderness Resort
3.0 star property
Indian Brook
7.0 out of 10, Good, (73 reviews)
"it was amazing. The location, the staff i strongly recomand"
Canada
Sylvie
The price is NZ$260
includes taxes & fees
21 Aug - 22 Aug
Cabot Shores Wilderness Resort
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Long Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Long Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Long Island. Seeing all the best attractions is bound to make you fall in love with Long Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Long Island short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find 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.

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

Full house: This holiday home rental outside of Long Island has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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

Bras d'Or Lake and Mouse Island are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Long Island and North Sydney Historical Society.

What’s a holiday rental in Long Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Long Island. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.