Holiday Homes in Long Island

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Featured Holiday Homes in Long Island

Fridge, microwave, oven, stovetop
Lakeview Luxury Retreat near Winnipesaukee lake

Lakeview Luxury Retreat near Winnipesaukee lake

Moultonborough
Lakeview Luxury Retreat near Winnipesaukee lake
Exterior
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 star property
Ashland
9.0 out of 10, Wonderful, (153)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
Cold Spring Plymouth Resort
Exterior
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

Freedom
8.8 out of 10, Excellent, (31)
"Didn't have a beach. Water access yes. Says in amenities has kayak there was none .Sent message about canoe never got combination for lock or were paddlers are. Sent message host about this before going .Property for most part comfortable. Some construction materials left around."
United States
Brian H.
The price is NZ$547
includes taxes & fees
7 Dec - 8 Dec
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
Terrace/patio
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Alton
9.6 out of 10, Exceptional, (24)
"Loved the dock access and location. Easy check in and out !"
United States
Destiny D.
The price is NZ$654
includes taxes & fees
20 Nov - 21 Nov
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Fridge, microwave, oven, stovetop
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath

Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath

Gilford
9.6 out of 10, Exceptional, (17)
"Nice property, suitable for our needs. "
United States
Katie H.
The price is NZ$1,097
includes taxes & fees
19 Nov - 20 Nov
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath
Property grounds
Lake Access + Kayaks + Arcade + Bike Path + Deck

Lake Access + Kayaks + Arcade + Bike Path + Deck

Wolfeboro
10.0 out of 10, Exceptional, (3)
"We had an absolutely wonderful stay at this property! This was our first time visiting NH and from the moment we arrived, we felt right at home. The house was spotlessly clean, beautifully decorated, and exactly as described in the listing.The location was ideal – peaceful and quiet, yet just a short drive from restaurants, shops, beach etc. The kitchen was fully equipped with everything we needed. It was clear the hosts put a lot of thought into the little details. We needed to use the kitchen...
United States
Juthika K.
The price is NZ$650
includes taxes & fees
16 Nov - 17 Nov
Lake Access + Kayaks + Arcade + Bike Path + Deck
Fridge, microwave, oven, stovetop
Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway

Gilford
10.0 out of 10, Exceptional, (71)
"Beautiful property. We enjoyed our trip."
United States
DEBORAH
The price is NZ$709
includes taxes & fees
17 Nov - 18 Nov
Idyllic Mountain and Lake Getaway
Exterior
Newly Renovated Post & Beam Style Barn.

Newly Renovated Post & Beam Style Barn.

Tamworth
10.0 out of 10, Exceptional, (13)
"Very nice stay, perfect place for me my wife and 2 dogs"
United States
Alex T.
The price is NZ$811
includes taxes & fees
1 Dec - 2 Dec
Newly Renovated Post & Beam Style Barn.
Terrace/patio
Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom

Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom

Holderness
10.0 out of 10, Exceptional, (1)
"Everything was wonderful!! "
United States
Scott O.
The price is NZ$648
includes taxes & fees
17 Nov - 18 Nov
Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom
Outdoor spa tub
Blue Breeze - Private lakefront w/ Hot Tub

Blue Breeze - Private lakefront w/ Hot Tub

Middleton
8.8 out of 10, Excellent, (3)
"This was a great property with a picture perfect view. We traveled here for my college graduation. We had no issues upon arrival other than the tv remotes not working and the downstairs door is still not able to lock, which appears to be an issue in a previous review. However, the downstairs bathroom began overflowing raw sewage one day into our stay. We placed towels down and contacted the host who within 30mins replied with a plumber would be out first thing in the morning. The following...
United States
Haley G.
The price is NZ$1,108
includes taxes & fees
17 Nov - 18 Nov
Blue Breeze - Private lakefront w/ Hot Tub
Smart TV, fireplace
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Sanbornton
10.0 out of 10, Exceptional, (13)
"We always find a house big enough for our two families to connect and visit while we attend Soulfest at Gunstock. This was close enough for us to go back and forth and provided a wonderful place for our families to eat, play games, sleep and enjoy being together. Hosts are amazing!! Super fast responses to questions. Quiet neighborhood and home was very clean and well kept. Highly recommend!"
United States
Jen O.
The price is NZ$1,229
includes taxes & fees
15 Nov - 16 Nov
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Property grounds
Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Wolfeboro
8.0 out of 10, Very good, (16)
"It was clean and fully lit up when we got there, with a bottle of wine waiting for us. We are not wine drinkers, but a nice gesture. It was a bit smaller than expected (I believe the photos make it appear bigger), but the LR furniture and queen bed were pretty comfortable (with no shortage of pillows). Having a comfortable bed always rates high on our list when looking for lodging and you never know what you’re going to get. There was, however, an odd noise (much like a random drip on a drum)...
United States
Patti D.
The price is NZ$606
includes taxes & fees
24 Nov - 25 Nov
Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Outdoor dining
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Gilford
10.0 out of 10, Exceptional, (2)
"Great place, new appliances, easy check in. Comfortable to watch huge tv. We had a wonderful time. Recommend highly."
United States
Cindy L.
The price is NZ$955
includes taxes & fees
16 Nov - 17 Nov
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location
Smart TV, fireplace, video games, ping pong
Baby Chocorua A Frame in the mountains sleeps 9

Baby Chocorua A Frame in the mountains sleeps 9

Chocorua
10.0 out of 10, Exceptional, (13)
"We had a wonderful time here- everyone from my 90 year old mother to my 10 year old daughter greatly enjoyed the place. It's clean, brand new, and includes all manner of thoughtful furnishings for a pleasant stay. The neighborhood is quiet and rural- we had a couple of barn owls courting outside in the front yard one night. It's also convenient to both the lakes region and the White Mountains, and White Lake State Park is literally only steps away.I would happily stay here again. "
United States
Greg E.
The price is NZ$855
includes taxes & fees
17 Nov - 18 Nov
Baby Chocorua A Frame in the mountains sleeps 9
Terrace/patio
Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage Central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom

Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage Central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom

Holderness
10.0 out of 10, Exceptional, (3)
"Our family enjoyed our week at this lovely home in December. The fireplace and hot tub provided endless enjoyment, the house was well appointed, and Ashely, the host, was very responsive and offered great suggestions as to where to explore!"
United States
Jessica T.
The price is NZ$1,642
includes taxes & fees
16 Nov - 17 Nov
Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage Central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom
Exterior
Gunstock Getaway | Hot Tub, Game Room & Near Lake

Gunstock Getaway | Hot Tub, Game Room & Near Lake

Gilford
The price is NZ$1,294
includes taxes & fees
24 Nov - 25 Nov
Gunstock Getaway | Hot Tub, Game Room & Near Lake
Terrace/patio
3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!

3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!

Laconia
9.0 out of 10, Wonderful, (4)
"The inside is beautiful and very clean . Lots of room and everything was well stocked. "
United States
Ariel G.
The price is NZ$588
includes taxes & fees
16 Nov - 17 Nov
3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!
Smart TV, DVD player, offices, computer monitors
Main St Location | Pets, Fenced Side Yard | Walk to Church Landing, Lake Winnipesaukee and Shops in minutes | BankNH Pavilion

Main St Location | Pets, Fenced Side Yard | Walk to Church Landing, Lake Winnipesaukee and Shops in minutes | BankNH Pavilion

Meredith
8.0 out of 10, Very good, (5)
"The pictures were not like i saw. The threads on the stairs were loose and someone could have fallen. Most of the chairs in the dining room were rickety. The place was big enough, but overall meh."
United States
Jean C.
The price is NZ$1,241
includes taxes & fees
17 Nov - 18 Nov
Main St Location | Pets, Fenced Side Yard | Walk to Church Landing, Lake Winnipesaukee and Shops in minutes | BankNH Pavilion
Outdoor dining
great location weirs beach area rental

great location weirs beach area rental

Weirs Beach
9.4 out of 10, Exceptional, (27)
"The house was very clean, beds comfortable, all the amenities away from home were available. We enjoyed the quiet, yet convenient to weirs beach pier. If in the area would stay again"
United Kingdom
Lisa S.
The price is NZ$1,316
includes taxes & fees
30 Nov - 1 Dec
great location weirs beach area rental
Fridge, microwave, oven, stovetop
Secluded Private 38 Acre Oasis

Secluded Private 38 Acre Oasis

Tamworth
9.0 out of 10, Wonderful, (2)
"Our group of 12 adults had no trouble being comfortable at this property. Plenty of space between the main house and cottage and outside."
United States
Evelyn B.
The price is NZ$1,777
includes taxes & fees
15 Nov - 16 Nov
Secluded Private 38 Acre Oasis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Long Island Hotel Reviews

Steele Hill Resorts

Steele Hill Resorts

10/10 Excellent
"Excellent as always. Everything was great except for the time that goes really fast when we’re enjoying so much. "
Tania 2-night trip
Posted 3 days ago
Steele Hill Resorts

Find out more about Long Island

Long Island Holiday Homes information

Number of reviews
Accommodation
 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia