Enter dates for more accurate prices
321 Holiday homes
Holiday cottage with swimming pool in Shelter Island Heights
Shelter Island / Shelter Island Heights
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Map
Add to shortlist
from £342 / night
Shelter Island holiday home rental
Hamptons / Shelter Island
4 8 14 nights min
- 4 bedrooms
- sleeps 8
- 14 nights min
- Nearest beach 1 km
- Child friendly
- Air conditioning
Map
Add to shortlist
from £262 / night
Shelter Island holiday home let
Hamptons / Shelter Island
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Map
Add to shortlist
from £439 / night
Shelter Island holiday home rental
Hamptons / Shelter Island
3 8 14 nights min
- 3 bedrooms
- sleeps 8
- 14 nights min
- Child friendly
- Air conditioning
- Private garden
Map
Add to shortlist
from £824 / night
Holiday villa in Shelter Island Heights
Shelter Island / Shelter Island Heights
6 12 7 nights min
- 6 bedrooms
- sleeps 12
- 7 nights min
- Ask owner if suitable for children
- Ask about pets
Map
Add to shortlist
from £3,097 / night
Great rentals within 20 miles that match your search
Distance approx 5.27 miles from Shelter Island
Holiday home in Sag Harbor
Hamptons / Sag Harbor
4 8 2 nights min
- 4 bedrooms
- sleeps 8
- 2 nights min
- Child friendly
- Air conditioning
Add to shortlist
from £665 / night
Distance approx 10.08 miles from Shelter Island
East Hampton holiday home rental
Hamptons / East Hampton
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Nearest beach 4 km
- Swimming pool
- Air conditioning
Add to shortlist
from £222 / night
Distance approx 4.3 miles from Shelter Island
Certificate of Excellence
Holiday apartment in Greenport
North Fork / Greenport
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 0 km
- Swimming pool
Certificate of Excellence
Add to shortlist
from £222 / night
Distance approx 6.95 miles from Shelter Island
Home accommodation in Orient
North Fork / Orient
5 14 14 nights min
- 5 bedrooms
- sleeps 14
- 14 nights min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £843 / night
Distance approx 16.46 miles from Shelter Island
Home letting in Hampton Bays with swimming pool
Southampton / Hampton Bays
4 9 14 nights min
- 4 bedrooms
- sleeps 9
- 14 nights min
- Nearest beach 3 km
- Swimming pool
- Child friendly
Add to shortlist
from £577 / night
Distance approx 10.13 miles from Shelter Island
Holiday cottage with shared pool in East Hampton
Hamptons / East Hampton
1 4 1 night min
- 1 bedroom
- sleeps 4
- 1 night min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £133 / night
Distance approx 10.86 miles from Shelter Island
Holiday home with golf nearby in East Hampton
Hamptons / East Hampton
3 6 1 night min
- 3 bedrooms
- sleeps 6
- 1 night min
- Beach / lakeside relaxation
- Swimming pool
- Child friendly
Add to shortlist
from £1,951 / night
Distance approx 5.04 miles from Shelter Island
Home rental in East Marion
North Fork / East Marion
4 8 7 nights min
- 4 bedrooms
- sleeps 8
- 7 nights min
- Child friendly
- Air conditioning
- Pet friendly
Add to shortlist
from £221 / night
Distance approx 13.85 miles from Shelter Island
Holiday home in Southampton
Hamptons / Southampton
4 8 14 nights min
- 4 bedrooms
- sleeps 8
- 14 nights min
- Beach / lakeside relaxation
- Air conditioning
- Private garden
Add to shortlist
from £1,583 / night
Distance approx 6.6 miles from Shelter Island
Holiday home in East Hampton
Hamptons / East Hampton
3 7 15 nights min
- 3 bedrooms
- sleeps 7
- 15 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £824 / night
Distance approx 14.11 miles from Shelter Island
Holiday apartment in Mattituck
North Fork / Mattituck
5 14 2 nights min
- 5 bedrooms
- sleeps 14
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 4 km
- Ask owner if suitable for children
Add to shortlist
from £794 / night
Distance approx 4.62 miles from Shelter Island
Holiday cottage in East Marion
North Fork / East Marion
2 4 1 night min
- 2 bedrooms
- sleeps 4
- 1 night min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £355 / night
Distance approx 4.52 miles from Shelter Island
East Marion holiday cottage rental
North Fork / East Marion
2 4 1 night min
- 2 bedrooms
- sleeps 4
- 1 night min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £355 / night
Distance approx 19.14 miles from Shelter Island
Holiday home in Montauk
Hamptons / Montauk
4 8 14 nights min
- 4 bedrooms
- sleeps 8
- 14 nights min
- Beach / lakeside relaxation
- Nearest beach 2 km
- Child friendly
Add to shortlist
from £887 / night
Distance approx 4.43 miles from Shelter Island
Holiday home in Southold
North Fork / Southold
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £412 / night
Distance approx 7.84 miles from Shelter Island
Peconic holiday cottage rental
North Fork / Peconic
3 6 14 nights min
- 3 bedrooms
- sleeps 6
- 14 nights min
- Beach / lakeside relaxation
- Child friendly
- Air conditioning
Add to shortlist
from £380 / night
Distance approx 7.26 miles from Shelter Island
Holiday home rental
Hamptons / Southampton
4 8 7 nights min
- 4 bedrooms
- sleeps 8
- 7 nights min
- Nearest beach 12 km
- Swimming pool
- Ask owner if suitable for children
Add to shortlist
from £570 / night
Distance approx 6.76 miles from Shelter Island
Holiday home with golf nearby in East Hampton
Hamptons / East Hampton
6 12 2 nights min
- 6 bedrooms
- sleeps 12
- 2 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £2,881 / night
Distance approx 7.26 miles from Shelter Island
Holiday private room with shared pool in Southampton
Hamptons / Southampton
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Nearest beach 12 km
- Swimming pool
- Air conditioning
Add to shortlist
from £222 / night
Distance approx 8.25 miles from Shelter Island
East Hampton holiday home rental
Hamptons / East Hampton
3 6 14 nights min
- 3 bedrooms
- sleeps 6
- 14 nights min
- Swimming pool
- Air conditioning
Add to shortlist
from £339 / night
Distance approx 15.13 miles from Shelter Island
Holiday apartment in Hampton Bays
Southampton / Hampton Bays
1 4 13 nights min
- 1 bedroom
- sleeps 4
- 13 nights min
- Air conditioning
- Private garden
Add to shortlist
from £178 / night
Distance approx 10.25 miles from Shelter Island
Holiday farmhouse in East Hampton
Hamptons / East Hampton
3 8 30 nights min
- 3 bedrooms
- sleeps 8
- 30 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £577 / night
Distance approx 4.56 miles from Shelter Island
Holiday home in East Marion
North Fork / East Marion
5 9 1 night min
- 5 bedrooms
- sleeps 9
- 1 night min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £843 / night
Distance approx 12.71 miles from Shelter Island
Holiday home in Southampton
Hamptons / Southampton
4 9 7 nights min
- 4 bedrooms
- sleeps 9
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £1,330 / night
Distance approx 9.98 miles from Shelter Island
Home rental in East Hampton
Hamptons / East Hampton
3 12 7 nights min
- 3 bedrooms
- sleeps 12
- 7 nights min
- Child friendly
- Air conditioning
- Pet friendly
Add to shortlist
from £317 / night
Distance approx 5.21 miles from Shelter Island
Sag Harbor holiday home rental
Hamptons / Sag Harbor
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £732 / night
Distance approx 9.33 miles from Shelter Island
Holiday home in East Hampton
Hamptons / East Hampton
4 8 7 nights min
- 4 bedrooms
- sleeps 8
- 7 nights min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £499 / night
Distance approx 9.26 miles from Shelter Island
Home rental in East Hampton
Hamptons / East Hampton
8 16 7 nights min
- 8 bedrooms
- sleeps 16
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £6,649 / night
Distance approx 16.31 miles from Shelter Island
Holiday home in Hampton Bays
Southampton / Hampton Bays
3 5 2 nights min
- 3 bedrooms
- sleeps 5
- 2 nights min
- Child friendly
- Air conditioning
- Pet friendly
Add to shortlist
from £333 / night
Distance approx 5.37 miles from Shelter Island
Holiday home letting
Hamptons / Sag Harbor
4 8 30 nights min
- 4 bedrooms
- sleeps 8
- 30 nights min
- Swimming pool
- Child friendly
- Car not necessary
Add to shortlist
from £1,478 / night
Distance approx 10.25 miles from Shelter Island
Holiday home in Springs
Hamptons / Springs
6 14 7 nights min
- 6 bedrooms
- sleeps 14
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £1,900 / night
Distance approx 6.59 miles from Shelter Island
Home rental in East Hampton
Hamptons / East Hampton
4 8 90 nights min
- 4 bedrooms
- sleeps 8
- 90 nights min
- Beach / lakeside relaxation
- Nearest beach 0.8 km
- Swimming pool
Add to shortlist
from £104 / night
Distance approx 8.23 miles from Shelter Island
Southampton holiday home rental
Hamptons / Southampton
4 10 14 nights min
- 4 bedrooms
- sleeps 10
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
Add to shortlist
from £710 / night
Distance approx 13.94 miles from Shelter Island
Hotel apartment rental in Southampton
Hamptons / Southampton
1 4 1 night min
- 1 bedroom
- sleeps 4
- 1 night min
- Child friendly
- Air conditioning
Add to shortlist
from £186 / night
Distance approx 4.67 miles from Shelter Island
East Marion holiday home rental
North Fork / East Marion
4 8 2 nights min
- 4 bedrooms
- sleeps 8
- 2 nights min
- Child friendly
- Air conditioning
- Private garden
Add to shortlist
from £577 / night
Page 1 of 1
1Also consider
- North America Holidays 202682 properties
- United States Holidays 157416 properties
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travellers.