Viewing 40 of 576 rentals in Southold
Tell us your dates, and we will find the most accurate rates and availability for you
Updating
Houses in Southold and Condos - Holiday Lettings - Holiday Rentals Southold
1 Holiday homes
Great rentals within 20 miles that match your search
from £2,743 / night
£19,199 / week
Great rentals within 20 miles that match your search
Holiday home in Middlefield
Middlefield house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £458 / night
£2,423 / week
Great rentals within 20 miles that match your search
Holiday home in Middlefield
Middlefield house
- 2 bedrooms
- 1 bathroom
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £115 / night
£1,143 / week
Great rentals within 20 miles that match your search
Holiday home in Montauk
Montauk house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £823 / night
£5,760 / week
Great rentals within 20 miles that match your search
Holiday home with golf nearby in East Hampton
East Hampton house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £2,012 / night
£11,428 / week
Great rentals within 20 miles that match your search
Home rental in Greenwich with golf nearby
Greenwich house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £320 / night
£2,240 / week
Great rentals within 20 miles that match your search
Home rental in Middletown
Middletown house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £320 / night
£2,012 / week
Great rentals within 20 miles that match your search
Holiday home in Narragansett
Narragansett house
- 4 bedrooms
- 2 bathrooms
- sleeps 9
1 filter does not match: Beach or lakeside relaxation
from £314 / night
£2,194 / week
Great rentals within 20 miles that match your search
Holiday home in Ocean Bay Park
Ocean Bay Park house
- 5 bedrooms
- 3 bathrooms
- sleeps 12
1 filter does not match: Beach or lakeside relaxation
from £2,012 / night
£11,428 / week
Great rentals within 20 miles that match your search
Home rental in Newport
Newport house
- 6 bedrooms
- 4 bathrooms
- sleeps 16
1 filter does not match: Beach or lakeside relaxation
from £823 / night
£6,400 - £7,168 / week
Great rentals within 20 miles that match your search
Middletown holiday apartment rental
Middletown apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 7
1 filter does not match: Beach or lakeside relaxation
from £458 / night
£2,743 / week
Great rentals within 20 miles that match your search
Holiday private room with shared pool in Southampton
Southampton private room
- 1 bedroom
- 1 bathroom
- sleeps 2
1 filter does not match: Beach or lakeside relaxation
from £284 / night
£1,984 / week
Great rentals within 20 miles that match your search
Holiday home with golf nearby in Narragansett
Narragansett house
- 4 bedrooms
- 2 bathrooms
- sleeps 9
1 filter does not match: Beach or lakeside relaxation
from £732 / night
£4,114 / week
Great rentals within 20 miles that match your search
Holiday home in East Hampton
East Hampton house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
1 filter does not match: Beach or lakeside relaxation
from £849 / night
£5,943 / week
Great rentals within 20 miles that match your search
Home rental in Southampton
Southampton house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £523 / night
£3,657 / week
Great rentals within 20 miles that match your search
Holiday home with swimming pool in East Hampton
East Hampton house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £915 / night
£5,029 / week
Great rentals within 20 miles that match your search
Holiday condo in Montauk
Montauk condo
- 1 bedroom
- 1 bathroom
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £458 / night
£3,200 / week
Great rentals within 20 miles that match your search
Holiday home in Southampton
Southampton house
- 4 bedrooms
- 5 bathrooms
- sleeps 9
1 filter does not match: Beach or lakeside relaxation
from £1,372 / night
£9,600 / week
Great rentals within 20 miles that match your search
Holiday condo in Newport
Newport condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £235 / night
£1,646 / week
Great rentals within 20 miles that match your search
Holiday home in Westport Point
Westport Point house
- 2 bedrooms
- 1 bathroom
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £431 / night
£3,017 / week
Great rentals within 20 miles that match your search
Roxbury holiday hotel apartment rental
Roxbury hotel apartment
- 2 bedrooms
- 1 bathroom
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £228 / night
£1,366 / week
Great rentals within 20 miles that match your search
Holiday home in East Hampton
East Hampton house
- 5 bedrooms
- 4 bathrooms
- sleeps 12
1 filter does not match: Beach or lakeside relaxation
from £915 / night
£6,400 / week
Great rentals within 20 miles that match your search
Holiday home in Greenport
Greenport house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £327 / night
£2,286 / week
Great rentals within 20 miles that match your search
Apartment rental in Stafford Springs
Stafford Springs apartment
- 1 bedroom
- 4 bathrooms
- sleeps 2
1 filter does not match: Beach or lakeside relaxation
from £138 / night
£960 / week
Great rentals within 20 miles that match your search
Holiday condo accommodation
Newport condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £389 / night
£2,720 / week
Great rentals within 20 miles that match your search
Holiday cottage rental
Southampton cottage
- 4 bedrooms
- 10 bathrooms
- sleeps 10
1 filter does not match: Beach or lakeside relaxation
from £2,612 / night
£18,285 / week
Great rentals within 20 miles that match your search
Holiday condo in Newport
Newport condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £418 / night
£2,926 / week
Great rentals within 20 miles that match your search
Amagansett holiday home rental
Amagansett house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £1,045 / night
£7,314 / week
Great rentals within 20 miles that match your search
Home rental in Southampton
Southampton house
- 5 bedrooms
- 5 bathrooms
- sleeps 12
1 filter does not match: Beach or lakeside relaxation
from £2,612 / night
£18,285 / week
Great rentals within 20 miles that match your search
East Hampton holiday home rental
East Hampton house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £784 / night
£5,486 / week
Great rentals within 20 miles that match your search
Newport holiday studio rental
Newport studio
- Studio
- 1 bathroom
- sleeps 4
1 filter does not match: Beach or lakeside relaxation
from £107 / night
£747 / week
Great rentals within 20 miles that match your search
Holiday home in East Hampton
East Hampton house
- 7 bedrooms
- 9 bathrooms
- sleeps 12
1 filter does not match: Beach or lakeside relaxation
from £9,795 / night
£68,566 / week
Great rentals within 20 miles that match your search
Home rental in Baiting Hollow
Baiting Hollow house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £639 / night
£4,474 / week
Great rentals within 20 miles that match your search
Holiday manor house rental
Bloomfield manor house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £732 / night
£3,657 / week
Great rentals within 20 miles that match your search
Montauk holiday manor house rental
Montauk manor house
- 5 bedrooms
- 8 bathrooms
- sleeps 10
1 filter does not match: Beach or lakeside relaxation
from £13,714 / night
£95,992 / week
Great rentals within 20 miles that match your search
Home accommodation in Orient
Orient house
- 4 bedrooms
- 3 bathrooms
- sleeps 6
1 filter does not match: Beach or lakeside relaxation
from £869 / night
£6,080 / week
Great rentals within 20 miles that match your search
Home rental in Hampton Bays
Hampton Bays house
- 8 bedrooms
- 6 bathrooms
- sleeps 20
1 filter does not match: Beach or lakeside relaxation
from £973 / night
£6,811 / week
Great rentals within 20 miles that match your search
Holiday farmhouse in East Hampton
East Hampton farmhouse
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 filter does not match: Beach or lakeside relaxation
from £869 / night
£6,080 / week
Great rentals within 20 miles that match your search
Holiday home in Southold
Southold house
- 4 bedrooms
- 2 bathrooms
- sleeps 10
1 filter does not match: Beach or lakeside relaxation
from £731 / night
£3,840 / week
Great rentals within 20 miles that match your search
Holiday private room rental
Springs private room
- 1 bedroom
- 2 bathrooms
- sleeps 2
1 filter does not match: Beach or lakeside relaxation
from £275 / night
£1,920 / week