Holiday Homes in Long Island

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Featured Holiday Homes in Long Island

Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is AU$1,467
per night
30 May - 31 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
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Interior
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, (1)
"I found it cozy, comfortable and very peaceful. Bonus wildlife visits of deer, geese and turkeys, Most people will understand this accommodation as quality “clamping”."
The price is AU$361
per night
19 May - 20 May
Airstream Art Studio Sculpture/Nature Preserve
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
10.0 out of 10, Exceptional, (33)
"Perfect location!"
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
A heated pool
Father’s Day Weekend Available. Beautiful 5br, pool, hot tub, private beach.
10.0 out of 10, Exceptional, (67)
"The house was great - just as listed and very comfortable / kid friendly. There wasn't a whole lot to do in the area over the holidays but we enjoyed the house, trampoline and jungle gym."
Father’s Day Weekend Available. Beautiful 5br, pool, hot tub, private beach.
Property grounds
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
10.0 out of 10, Exceptional, (10)
"Perfect spot for a weekend on the North Fork"
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Interior
Weekend Special May 1-June 15 includes gift certificate to East Hampton Grill.
10.0 out of 10, Exceptional, (16)
"This place was great all around, really nice open kitchen and sunset by the pool in the backyard was very serene; easy to get into town, the beach, Sag harbor, Amagansett, really great location within East Hampton"
Weekend Special May 1-June 15 includes gift certificate to East Hampton Grill.
On the beach
Entire, new, roomy, village beach house close to beach, park, and town center
10.0 out of 10, Exceptional, (10)
"This was a great house! Everythingwas perfect, the house was very clean and David was incredibly accomodating to all our requests and provifed great recommendations for places to visit. We will definitely be back"
Entire, new, roomy, village beach house close to beach, park, and town center
Fridge, oven, stovetop, dishwasher
Cozy queen-size room with private bathroom in BedStuy
10.0 out of 10, Exceptional, (2)
"We had a very good time. Emanuele and Francesco were very welcoming and gave us good tips to discover the city. Yuki and Lenu are lovely cats <3. The location is in a quiet neighborhood and close to the subway, making it very easy to go to Manhattan. I recommend this place and would stay again."
Cozy queen-size room with private bathroom in BedStuy
View from property
Newly renovated 5mins walk from best surf beach Ditch!
10.0 out of 10, Exceptional, (3)
"Melody's house was so enjoyable, in a quiet neighborhood, beautifully renovated with high-end kitchen and bathrooms, light and airy living room. My son is a chef and found the kitchen super well equipped. We've been coming to Montauk many years and this is the first rental we look forward to repeating!"
Newly renovated 5mins walk from best surf beach Ditch!
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Interior
Charming cottage in the heart of the North Fork
9.8 out of 10, Exceptional, (36)
"This cottage is Comfortable, clean and fully stocked on a private street with a beautiful short walk to the beach. We were only 2 but house could easily sleep up to 8 guests. Large backyard with tranquil outdoor setting firepit and Barbeque. Host is very responsive welcoming and helpful. The nearby Main street has many restaurants and shops as well as Wine vineyards. Will definitely be booking again in future. We found a new love and that is Jamesport. Thank you Kelly!"
Charming cottage in the heart of the North Fork
Outdoor dining
LA MAISON DES SIRENES 1, Bohemian and charm,ing 20mn away from city.
9.6 out of 10, Exceptional, (87)
"Nathalie was really great with communicating during my stay. It was an awesome location with a really cozy vibe inside. Super unique and much better than just staying in a hotel. Would definitely stay here again"
LA MAISON DES SIRENES 1, Bohemian and charm,ing 20mn away from city.
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
A heated pool
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
9.6 out of 10, Exceptional, (5)
"Beautiful, well appointed new construction in desirable Greenport area. Minutes to local vineyards and the shoreline. Comfortable for 3 couples. Kitchen was perfect for simple meals. Off season, so we didn’t get to use the pool but it looked amazing!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
Microwave, oven, stovetop, coffee/tea maker
Expansive Decking, Large Pool, Perfect for Entertaining, Close to East...
9.6 out of 10, Exceptional, (21)
"Very nice house that has everything you need. We have 4 couples stay for a long weekend. Plenty of room for everyone. Easy walk into town. We really enjoyed hanging by the pool in the backyard. Would definitely rent this property again."
Expansive Decking, Large Pool, Perfect for Entertaining, Close to East...
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Property grounds
The SandPiper
9.4 out of 10, Exceptional, (3)
"This listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"
The SandPiper
Property grounds
West End Dream Home
9.4 out of 10, Exceptional, (10)
"Great West End Long Beach location, clean, good communication with host, great parking under living space. We had a wonderful family vacation!"
West End Dream Home
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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.

Other property types in Long Island

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is AU$286
per night
20 May - 21 May
Montauk Manor
Deluxe Studio Suite | Private kitchen
Starlight Hotel
2.0 star property
9.0 out of 10, Wonderful, (125)
"It was very clean. Options for breakfast were limited."
The price is AU$274
per night
29 May - 30 May
Starlight Hotel
Rooftop terrace
Sonder The Dutch
3.5 star property
8.8 out of 10, Excellent, (60)
"The hotel itself was amazing, clean, staff were friendly and helpful, the views from the hotel were breathtaking - it was located quite close to three different subway stations. Sonder is 10/10. "
The price is AU$387
per night
11 June - 12 June
Sonder The Dutch
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.

Long Island Holiday Homes information

Number of reviews
362
Accommodation
292 Holiday Homes
Lowest Price
AU$167
Highest Price
AU$1,467

Recent Reviews in Long Island
Expedia verified reviews