Long Island holiday lettings

We found 1,031 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Long Island

Showing deals for:25 Dec - 1 Jan

The lower level which walks out to firepit area
Eat in kitchen
Great LARGE  private fire pit!
Living room
Exceptional
(53 reviews)

1.5 miles to Gunstock. Great for larger groups or multiple families

Gilford

8% off
£2,693
for 7 nights, 1 chalet
£385 per night
includes taxes & fees
1.5 miles to Gunstock. Great for larger groups or multiple families
Living area
Exterior
Dining
Interior
Exceptional
(27 reviews)

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Laconia

8% off
£10,767
for 7 nights, 1 home
£1,538 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Room
Gather by the Firepit
Living area
Exterior
Wonderful
(51 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
£4,551
for 7 nights, 1 home
£650 per night
includes taxes & fees
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Property from end of dock
Property from the lake
Master Bedroom
Family room
Exceptional
(157 reviews)

Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more

Alton Bay

8% off
£4,389
for 7 nights, 1 home
£627 per night
includes taxes & fees
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
Golf
sitting on deck overlooking diamond, rattlesnake island and Wolfboro neck
view from kitchen
Private kitchen
Exceptional
(171 reviews)

Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile

Gilford

7% off
£2,675
for 7 nights, 1 home
£382 per night
includes taxes & fees
Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile
Living area
Dining
Private kitchen
Outdoor dining
Exceptional
(10 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
£7,371
for 7 nights, 1 home
£1,053 per night
includes taxes & fees
Spacious Lakes Region Retreat—Game Room & Gazebo
Private kitchen
Interior
Exterior detail
Dining area
Exceptional
(28 reviews)

Easiest Location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith

Meredith

8% off
£5,217
for 7 nights, 1 home
£745 per night
includes taxes & fees
Easiest Location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
Room
Living area
Dining
Private kitchen
Exceptional
(10 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
£2,353
for 7 nights, 1 cottage
£336 per night
includes taxes & fees
Quiet Lake Retreat with Fireplace and short walk to the beach
Fall colors overlooking the lake from the deck October 2022
Sunroom 4 Season
Private kitchen
4 season sunroom :-)
Exceptional
(26 reviews)

Kayak, walk or swim to Meredith town center

Meredith

8% off
£5,580
for 7 nights, 1 home
£797 per night
includes taxes & fees
Kayak, walk or swim to Meredith town center
Private kitchen
Private kitchen
Property grounds
Marina
Exceptional
(16 reviews)

NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE

Wolfeboro

8% off
£4,664
for 7 nights, 1 home
£666 per night
includes taxes & fees
NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE
Exterior
Comfy seats around one of two fire pits.
View of the house from the beach.
Interior
Exceptional
(189 reviews)

Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey

Moultonborough

8% off
£2,278
for 7 nights, 1 home
£325 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Property grounds
Castle in the clouds
Cable TV!!
Wonderful
(36 reviews)

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6

Moultonborough

8% off
£1,599
for 7 nights, 1 home
£228 per night
includes taxes & fees
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
Exterior
Pool
Property grounds
Property grounds
Exceptional
(11 reviews)

4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7

Laconia

8% off
£1,168
for 7 nights, 1 home
£167 per night
includes taxes & fees
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Private kitchen
Exterior
Property grounds
Living area
Exceptional
(24 reviews)

Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct

Gilford

8% off
£4,374
for 7 nights, 1 home
£625 per night
includes taxes & fees
Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct
Interior
Private kitchen
Living area
Interior
Exceptional
(10 reviews)

Cozy 4-Season Chalet + Lake Winni + Gunstock + Free Breakfast · Sleeps 8

Gilford

8% off
£2,257
for 7 nights, 1 home
£322 per night
includes taxes & fees
Cozy 4-Season Chalet + Lake Winni + Gunstock + Free Breakfast · Sleeps 8
Interior
Marina
Property grounds
Interior
Wonderful
(12 reviews)

Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's

Laconia

8% off
£1,672
for 7 nights, 1 apartment
£239 per night
includes taxes & fees
Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's
Dining
Exterior
Interior
Private kitchen
Exceptional
(53 reviews)

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

Meredith

8% off
£1,734
for 7 nights, 1 home
£248 per night
includes taxes & fees
Meredith Bay - Brand New 1st Floor Apartment In Private Home
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Long Island getaway

Learn about the unique charm of Long Island with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Long Island

Do you want to find top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Long Island a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Ellacoya State Park (5.2 mi / 8.4 km)
  • Wolfeboro Abenaki Ski Area (6.2 mi / 10 km)
  • Gunstock Mountain Resort (7.4 mi / 11.9 km)
  • Cascade Spa (7.6 mi / 12.2 km)
  • Stand Up Paddleboard NH (13 mi / 20.9 km)
  • Squam Lakes Natural Science Center (13.6 mi / 21.9 km)

Exploring the natural features in Long Island

Whether you're an adventurous traveller or just want to take in the scenery, Long Island is a great spot to appreciate mother nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Lake Winnipesaukee (2.8 mi / 4.6 km)
  • Ellacoya State Park (5.2 mi / 8.4 km)
  • Weirs Beach (6.3 mi / 10.1 km)
  • Endicott Rock Park (6.3 mi / 10.2 km)
  • Paugus Bay (7.8 mi / 12.5 km)
  • Lake Waukewan (9 mi / 14.5 km)

Frequently asked questions

What is the most popular type of holiday rental accommodation in Long Island?
Houses are the most popular type of holiday rental in Long Island, according to our data. Even if you have a different vision in mind, Vrbo has holiday homes in a variety of shapes and sizes. Take a look at our options to find your perfect match.
How much does it cost to rent a holiday rental in Long Island?
Several things influence what you'll pay for your holiday rental in Long Island, including the time of year, length of stay and property type. Still, all Vrbo homes have something in common — unbeatable value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Long Island?
The average price for a holiday home near the beach in Long Island depends on when you're going and the style and size of property you're searching for. Find prices quickly and easily on Vrbo by entering your travel dates and destination. Then use the filter tool to pick the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.
What are popular rental amenities in Long Island?
Two of the most in-demand rental amenities in Long Island are a microwave oven and a barbecue grill. Whether you're on a solo adventure, with family or a bunch of pals, there's a Vrbo holiday rental for everyone's needs.
Are there large group holiday rentals in Long Island?
Pick from four holiday properties in Long Island that can accommodate 10 or more guests. Whether you're organising a trip with the family or a special event like a birthday party, there's plenty of room to get your group together under the same roof.
Can I find two-bedroom holiday rentals in Long Island?
Long Island has five two-bedroom holiday rentals for you to select from. Book a holiday home with all the comfort and privacy you need at a price that's hard to resist on Vrbo.
How old do you have to be to rent a holiday rental in Long Island?
You'll have to check with the Long Island holiday home you'd like on Vrbo as the minimum age varies. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Long Island for?
The amount of time you can book a Long Island holiday home for depends on each property. Just enter your dates of travel to find options offering longer term stays. They have all you need to make your extended holiday more enjoyable such as kitchens and backyards. Some Vrbo holiday rentals may also offer discounted weekly or monthly prices, so you can stay even longer for less.

More holiday ideas