Walking holiday villas and apartments Long Island | Holiday Lettings

Close

View larger map

Also consider

North America Holidays
163164 properties
United States Holidays
118028 properties
Houses Hamptons
228 properties
North Fork
30 properties
Holiday rentals Fire Island
12 properties
Westhampton Beach
9 properties
Long Beach
6 properties

Long Island

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

39 Holiday homes

Filters applied: Walking holidays

Travellers going to Long Island are booking May dates now. Secure your holiday home today and have the perfect trip.

14

Long Island holiday cottage rental

Long Island / Fire Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Fire Island is a 35mile long barrier island located just off the South Shore of New York's Long Island. It is an island of many diverse communities. The house is located in a community called Lonelyville, one of the oldest on Fire Island. There are no cars permitte  …see more

from £530 / night

£3710 / week

Book View

from £530 / night

(9) Excellent 

18

North Fork / Cutchogue

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

 …see more

from £121 / night

£767 - £1638 / week

Book View

from £121 / night

29

Long Island / Shirley

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

 …see more

from £484 / night

£2904 - £4936 / week

Book View

from £484 / night

13

North Fork / Mattituck

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Ask owner if suitable for children

 …see more

from £722 / night

£2823 - £7339 / week

Book View

from £722 / night

(1) Excellent 

22

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

 …see more

from £238 / night

£1593 - £5081 / week

Book View

from £238 / night

18

Hamptons / Montauk

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

 …see more

from £404 / night

£2420 - £4839 / week

Book View

from £404 / night

(4) Excellent 

21

Hamptons / Sag Harbor

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £400 / night

£2097 - £2380 / week

Book View

from £400 / night

15

Long Island / Long Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Car not necessary

 …see more

from £242 / night

£968 - £1775 / week

Book View

from £242 / night

(4) Excellent 

28

Hamptons / Sag Harbor

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

 …see more

from £1729 / night

£12097 / week

Book View

from £1729 / night

(3) Excellent 

71

Hamptons / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 11 km
  • Swimming pool

 …see more

from £646 / night

£4436 - £5000 / week

Book View

from £646 / night

(1) Excellent 

7

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £299 / night

£2097 - £4759 / week

Book View

from £299 / night

(2) Very Good 

20

Hamptons / Bridgehampton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly

 …see more

from £109 / night

£763 - £932 / week

Book View

from £109 / night

(1) Excellent 

18

Long Island / Glen Cove

5 9 5 nights min

  • 5 bedrooms
  • Sleeps 9
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

 …see more

from £444 / night

£3359 - £3924 / week

Book View

from £444 / night

8

North Fork / Greenport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from £323 / night

£2259 / week

Book View

from £323 / night

15

Hamptons / Amagansett

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

 …see more

from £404 / night

£807 - £3428 / week

Book View

from £404 / night

(1) Very Good 

6

Long Island / Great Neck

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Ask owner if suitable for children

 …see more

from £121 / night

£646 - £871 / week

Book View

from £121 / night

18

Hamptons / East Quogue

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Swimming pool

 …see more

from £577 / night

£4033 / week

Book View

from £577 / night

(5) Very Good 

11

North Fork / Greenport

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

 …see more

from £174 / night

£1250 - £2097 / week

Book View

from £174 / night

20

Hamptons / East Hampton

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from £922 / night

£6452 / week

Book View

from £922 / night

(5) Average 

14

Long Island / Baiting Hollow

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

 …see more

from £142 / night

£847 / week

Book View

from £142 / night

20

Hamptons / Wainscott

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £1452 / night

£7259 / week

Book View

from £1452 / night

16

North Fork / Greenport

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £417 / night

£2917 / week

Book View

from £417 / night

(1) Excellent 

31

Hamptons / Hampton Bays

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

 …see more

from £524 / night

£3646 - £5009 / week

Book View

from £524 / night

35

Hamptons / Shelter Island

4 11 2 nights min

  • 4 bedrooms
  • Sleeps 11
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Ask owner if suitable for children

 …see more

from £1130 / night

£2823 / week

Book View

from £1130 / night

16

Hamptons / Montauk

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £807 / night

£5646 / week

Book View

from £807 / night

20

Hamptons / Amagansett

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £1748 / night

£12232 / week

Book View

from £1748 / night

(1) Very Good 

10

Hamptons / Water Mill

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

 …see more

from £549 / night

£4033 / week

Book View

from £549 / night

12

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £254 / night

£1775 / week

Book View

from £254 / night

24

Hamptons / East Hampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £1153 / night

£8065 / week

Book View

from £1153 / night

7

Hamptons / East Quogue

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Air conditioning

 …see more

from £61 / night

£323 / week

Book View

from £61 / night

16

Hamptons / Southampton

5 12 14 nights min

  • 5 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £1556 / night

£10888 / week

Book View

from £1556 / night

11

Hamptons / East Hampton

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £807 / night

£5646 / week

Book View

from £807 / night

13

Hamptons / East Hampton

3 8 14 nights min

  • 3 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £968 / night

£6775 / week

Book View

from £968 / night

15

Hamptons / East Hampton

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

 …see more

from £519 / night

£3630 / week

Book View

from £519 / night

(1) Excellent 

24

Long Island / Mastic Beach

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 17 km
  • Child friendly

 …see more

from £404 / night

£2823 / week

Book View

from £404 / night

15

Hamptons / East Hampton

5 9 3 nights min

  • 5 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £1210 / night

£8468 / week

Book View

from £1210 / night

39

Hamptons / Sag Harbor

4 10 90 nights min

  • 4 bedrooms
  • Sleeps 10
  • 90 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from £686 / night

£4799 / week

Book View

from £686 / night

12

Riverhead / Aquebogue

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from £323 / night

£1130 - £2178 / week

Book View

from £323 / night

24

Hamptons / Southampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £242 / night

£1694 / week

Book View

from £242 / night