Search Holiday Homes in Long Island

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Long Island holiday homes

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (190 reviews)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
The price is £82
includes taxes & fees
12 Mar - 13 Mar
Cold Spring Plymouth Resort

Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
9.8 out of 10, Exceptional, (45 reviews)
"Very clean and very comfortable. Short walk to downtown made our stay perfect. "
United States
Julian G.
The price is £230
includes taxes & fees
1 Mar - 2 Mar
Meredith Bay - Brand New 1st Floor Apartment In Private Home

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
The price is £428
includes taxes & fees
4 Mar - 5 Mar
[NEW] Cozy Cabin near Gunstock & Lake Winni

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is £161
includes taxes & fees
2 Mar - 3 Mar
Stunning Lake Views close to Weirs Beach & Gunstock

large-group mountain/lake getaway

large-group mountain/lake getaway
Gilford
9.6 out of 10, Exceptional, (18 reviews)
"We were very pleased with accommodations. We are 4 adults and the house had everything we needed for our visit. The beds were comfortable and the house was very clean. All communication with the host was answered quickly."
United States
Ruth R.
The price is £458
includes taxes & fees
27 Feb - 28 Feb
large-group mountain/lake getaway

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, (17 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is £258
includes taxes & fees
27 Feb - 28 Feb
Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great location, easy access and very clean. The only negative was the paper-thin walls or should I say neighbors that did not think of anyone else or their neighbors."
United States
Lisa D.
The price is £273
includes taxes & fees
11 Mar - 12 Mar
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Cozy Cabin near Tuftonboro & Lake Winnipesaukee
Tuftonboro
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property "
United States
Keith B.
The price is £328
includes taxes & fees
3 Mar - 4 Mar
Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway
Gilford
10.0 out of 10, Exceptional, (73 reviews)
"Amazing spot!"
United States
David E.
The price is £456
includes taxes & fees
4 Mar - 5 Mar
Idyllic Mountain and Lake Getaway

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 reviews)
"It was great and the weather was perfect. Love that it’s dog friendly! And Helen was very helpful. "
United States
ELIZABETH B T.
The price is £246
includes taxes & fees
3 Mar - 4 Mar
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

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, (14 reviews)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
The price is £495
includes taxes & fees
27 Feb - 28 Feb
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Lake Access + Kayaks + Arcade + Bike Path + Deck

Lake Access + Kayaks + Arcade + Bike Path + Deck
Wolfeboro
10.0 out of 10, Exceptional, (3 reviews)
"What you see is what you get and that's a very good thing!"
United States
john a.
The price is £236
includes taxes & fees
1 Mar - 2 Mar
Lake Access + Kayaks + Arcade + Bike Path + Deck

Cedar Lodge Condo w/ Loft and private balcony

Cedar Lodge Condo w/ Loft and private balcony
Weirs Beach
The price is £154
includes taxes & fees
27 Feb - 28 Feb
Cedar Lodge Condo w/ Loft and private balcony

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| 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| Main Level Bedroom and Bathroom
Holderness
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean and nice. "
United States
Bryan K.
The price is £616
includes taxes & fees
11 Mar - 12 Mar
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| Main Level Bedroom and Bathroom

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
New Durham
10.0 out of 10, Exceptional, (2 reviews)
"Suxhh a beautiful and well kept home. Relaxing there was our favorite part of the trip!"
United States
Justin G.
The price is £324
includes taxes & fees
3 Mar - 4 Mar
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

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

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location
Gilford
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
United States
dave b.
The price is £364
includes taxes & fees
1 Mar - 2 Mar
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location

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 review)
"Everything was wonderful!! "
United States
Scott O.
The price is £304
includes taxes & fees
3 Mar - 4 Mar
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

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
Gilmanton
The price is £511
includes taxes & fees
3 Mar - 4 Mar
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock

The Winterbrook Mountain House. Owls Nest Golf-Waterville Valley

The Winterbrook Mountain House. Owls Nest Golf-Waterville Valley
Campton
9.0 out of 10, Wonderful, (2 reviews)
"Winterbrook is a lovely property.Welcoming, clean and private.Very well maintained with all necessities available.Our son got married at the Owl’s Nest Resort and the home was nearby and easy to get to and from.Highly recommend!!"
United States
Katherine C.
The price is £393
includes taxes & fees
3 Mar - 4 Mar
The Winterbrook Mountain House. Owls Nest Golf-Waterville Valley

5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views

5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views
Gilford
10.0 out of 10, Exceptional, (12 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is £598
includes taxes & fees
3 Mar - 4 Mar
5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views
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.

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Long Island Hotel Reviews

Find out more about Long Island

Long Island Holiday Homes information

Number of reviews
363
Accommodation
823 Holiday Homes
Lowest Price
£82
Highest Price
£616

Explore a world of travel with Expedia