We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Helmsley Family & Kid Friendly Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
66 rentals in Helmsley.
Pinfold Cottage, vacation rental in Helmsley
Pinfold Cottage, vacation rental in Helmsley
Pinfold Cottage, vacation rental in Helmsley

Pinfold Cottage

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Cherry Tree House, vacation rental in Helmsley
Cherry Tree House, vacation rental in Helmsley
Cherry Tree House, vacation rental in Helmsley

Cherry Tree House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Forge Cottage, vacation rental in Helmsley
Forge Cottage, vacation rental in Helmsley
Forge Cottage, vacation rental in Helmsley

Forge Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
CASTLE VIEW, pet friendly, character holiday cottage, with a garden in, vacation rental in Helmsley
CASTLE VIEW, pet friendly, character holiday cottage, with a garden in, vacation rental in Helmsley
CASTLE VIEW, pet friendly, character holiday cottage, with a garden in, vacation rental in Helmsley

CASTLE VIEW, pet friendly, character holiday cottage, with a garden in

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
PEG'S COTTAGE, detached, ground floor, WiFi, gas fire, garden with furniture, vacation rental in Helmsley
PEG'S COTTAGE, detached, ground floor, WiFi, gas fire, garden with furniture, vacation rental in Helmsley
PEG'S COTTAGE, detached, ground floor, WiFi, gas fire, garden with furniture, vacation rental in Helmsley

PEG'S COTTAGE, detached, ground floor, WiFi, gas fire, garden with furniture

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
8 POTTERGATE MEWS, terraced, enclosed garden, in Helmsley, Ref 956799, vacation rental in Helmsley
8 POTTERGATE MEWS, terraced, enclosed garden, in Helmsley, Ref 956799, vacation rental in Helmsley
8 POTTERGATE MEWS, terraced, enclosed garden, in Helmsley, Ref 956799, vacation rental in Helmsley

8 POTTERGATE MEWS, terraced, enclosed garden, in Helmsley, Ref 956799

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
WETHERCOTE COTTAGE, family friendly, character holiday cottage, with a garden, vacation rental in Helmsley
WETHERCOTE COTTAGE, family friendly, character holiday cottage, with a garden, vacation rental in Helmsley
WETHERCOTE COTTAGE, family friendly, character holiday cottage, with a garden, vacation rental in Helmsley

WETHERCOTE COTTAGE, family friendly, character holiday cottage, with a garden

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
CORONATION COTTAGE, woodburner, wet room, all ground floor, fantastic location, vacation rental in Helmsley
CORONATION COTTAGE, woodburner, wet room, all ground floor, fantastic location, vacation rental in Helmsley
CORONATION COTTAGE, woodburner, wet room, all ground floor, fantastic location, vacation rental in Helmsley

CORONATION COTTAGE, woodburner, wet room, all ground floor, fantastic location

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
AUBURN HOUSE, detached, woodburning stove, near Helmsley, ref:943848, vacation rental in Helmsley
AUBURN HOUSE, detached, woodburning stove, near Helmsley, ref:943848, vacation rental in Helmsley
AUBURN HOUSE, detached, woodburning stove, near Helmsley, ref:943848, vacation rental in Helmsley

AUBURN HOUSE, detached, woodburning stove, near Helmsley, ref:943848

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
IVY COTTAGE, end-terrace, WiFi, lawned garden, close to town centre, in, vacation rental in Helmsley
IVY COTTAGE, end-terrace, WiFi, lawned garden, close to town centre, in, vacation rental in Helmsley
IVY COTTAGE, end-terrace, WiFi, lawned garden, close to town centre, in, vacation rental in Helmsley

IVY COTTAGE, end-terrace, WiFi, lawned garden, close to town centre, in

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
BELLWETHER, WiFi, open-plan, near Helmsley, vacation rental in Helmsley
BELLWETHER, WiFi, open-plan, near Helmsley, vacation rental in Helmsley
BELLWETHER, WiFi, open-plan, near Helmsley, vacation rental in Helmsley

BELLWETHER, WiFi, open-plan, near Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
3 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Rievaulx, near Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
29 Bondgate, Helmsley, vacation rental in Helmsley
29 Bondgate, Helmsley, vacation rental in Helmsley
29 Bondgate, Helmsley, vacation rental in Helmsley

29 Bondgate, Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Bilsdale, near Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
1 bedroom accommodation in Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
29 BONDGATE, pet friendly, character holiday cottage in Helmsley, vacation rental in Helmsley
29 BONDGATE, pet friendly, character holiday cottage in Helmsley, vacation rental in Helmsley
29 BONDGATE, pet friendly, character holiday cottage in Helmsley, vacation rental in Helmsley

29 BONDGATE, pet friendly, character holiday cottage in Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Kirkdale Cottage: a Hidden Gem, Helmsley (country cottage, sleeps 5), vacation rental in Helmsley
Kirkdale Cottage: a Hidden Gem, Helmsley (country cottage, sleeps 5), vacation rental in Helmsley
Kirkdale Cottage: a Hidden Gem, Helmsley (country cottage, sleeps 5), vacation rental in Helmsley

Kirkdale Cottage: a Hidden Gem, Helmsley (country cottage, sleeps 5)

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 VALLEY VIEW LODGES, family friendly, with a garden in Helmsley, vacation rental in Helmsley
3 VALLEY VIEW LODGES, family friendly, with a garden in Helmsley, vacation rental in Helmsley
3 VALLEY VIEW LODGES, family friendly, with a garden in Helmsley, vacation rental in Helmsley

3 VALLEY VIEW LODGES, family friendly, with a garden in Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
AUBURN HOUSE, family friendly, with open fire in Beadlam, vacation rental in Helmsley
AUBURN HOUSE, family friendly, with open fire in Beadlam, vacation rental in Helmsley
AUBURN HOUSE, family friendly, with open fire in Beadlam, vacation rental in Helmsley

AUBURN HOUSE, family friendly, with open fire in Beadlam

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Central Modern open plan house 3 ensuite bedrooms, dog friendly., vacation rental in Helmsley
Central Modern open plan house 3 ensuite bedrooms, dog friendly., vacation rental in Helmsley
Central Modern open plan house 3 ensuite bedrooms, dog friendly., vacation rental in Helmsley

Central Modern open plan house 3 ensuite bedrooms, dog friendly.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
2 bedroom accommodation in Helmsley, near York, vacation rental in Helmsley
2 bedroom accommodation in Helmsley, near York, vacation rental in Helmsley
2 bedroom accommodation in Helmsley, near York, vacation rental in Helmsley

2 bedroom accommodation in Helmsley, near York

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
The Annex - Central Helmsley with parking, vacation rental in Helmsley
The Annex - Central Helmsley with parking, vacation rental in Helmsley
The Annex - Central Helmsley with parking, vacation rental in Helmsley

The Annex - Central Helmsley with parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
4 bedroom accommodation in Old Byland, near Helmsley, vacation rental in Helmsley
4 bedroom accommodation in Old Byland, near Helmsley, vacation rental in Helmsley
4 bedroom accommodation in Old Byland, near Helmsley, vacation rental in Helmsley

4 bedroom accommodation in Old Byland, near Helmsley

Rental Home
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Bilsdale, near Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Cliff House, Helmsley, vacation rental in Helmsley
Cliff House, Helmsley, vacation rental in Helmsley
Cliff House, Helmsley, vacation rental in Helmsley

Cliff House, Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
3 Valley View Lodges, Helmsley, vacation rental in Helmsley
3 Valley View Lodges, Helmsley, vacation rental in Helmsley
3 Valley View Lodges, Helmsley, vacation rental in Helmsley

3 Valley View Lodges, Helmsley

Cabin
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
1 bedroom accommodation in Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Bilsdale, near Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
2 bedroom accommodation in Helmsley, York, vacation rental in Helmsley
2 bedroom accommodation in Helmsley, York, vacation rental in Helmsley
2 bedroom accommodation in Helmsley, York, vacation rental in Helmsley

2 bedroom accommodation in Helmsley, York

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Helmsley

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Host & Stay | Willow Cottage, vacation rental in Helmsley
Host & Stay | Willow Cottage, vacation rental in Helmsley
Host & Stay | Willow Cottage, vacation rental in Helmsley

Host & Stay | Willow Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
2 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley

2 bedroom accommodation in Bilsdale, near Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Helmsley

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
CLIFF HOUSE, family friendly, character holiday cottage in Helmsley, vacation rental in Helmsley
CLIFF HOUSE, family friendly, character holiday cottage in Helmsley, vacation rental in Helmsley
CLIFF HOUSE, family friendly, character holiday cottage in Helmsley, vacation rental in Helmsley

CLIFF HOUSE, family friendly, character holiday cottage in Helmsley

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
WETHERCOTE COTTAGE, pet friendly, with a garden in Helmsley, vacation rental in Helmsley
WETHERCOTE COTTAGE, pet friendly, with a garden in Helmsley, vacation rental in Helmsley
WETHERCOTE COTTAGE, pet friendly, with a garden in Helmsley, vacation rental in Helmsley

WETHERCOTE COTTAGE, pet friendly, with a garden in Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Riverbank Apartment, Helmsley, vacation rental in Helmsley
Riverbank Apartment, Helmsley, vacation rental in Helmsley
Riverbank Apartment, Helmsley, vacation rental in Helmsley

Riverbank Apartment, Helmsley

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
3 bedroom accommodation in York, vacation rental in Helmsley
3 bedroom accommodation in York, vacation rental in Helmsley
3 bedroom accommodation in York, vacation rental in Helmsley

3 bedroom accommodation in York

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Bay tree Cottage Helmsley North Yorkshire, vacation rental in Helmsley
Bay tree Cottage Helmsley North Yorkshire, vacation rental in Helmsley
Bay tree Cottage Helmsley North Yorkshire, vacation rental in Helmsley

Bay tree Cottage Helmsley North Yorkshire

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
The Old Post Office - Central Helmsley with parking, vacation rental in Helmsley
The Old Post Office - Central Helmsley with parking, vacation rental in Helmsley
The Old Post Office - Central Helmsley with parking, vacation rental in Helmsley

The Old Post Office - Central Helmsley with parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
2 bedroom accommodation in near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in near Helmsley, vacation rental in Helmsley

2 bedroom accommodation in near Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Cottage In Helmsley, North Yorkshire Moors, England, vacation rental in Helmsley
Cottage In Helmsley, North Yorkshire Moors, England, vacation rental in Helmsley
Cottage In Helmsley, North Yorkshire Moors, England, vacation rental in Helmsley

Cottage In Helmsley, North Yorkshire Moors, England

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Cygnet Cottage, vacation rental in Helmsley
Cygnet Cottage, vacation rental in Helmsley
Cygnet Cottage, vacation rental in Helmsley

Cygnet Cottage

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
3 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Rievaulx, near Helmsley

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Rye Court Cottage - Stunning cottage in central Helmsley with parking, vacation rental in Helmsley
Rye Court Cottage - Stunning cottage in central Helmsley with parking, vacation rental in Helmsley
Rye Court Cottage - Stunning cottage in central Helmsley with parking, vacation rental in Helmsley

Rye Court Cottage - Stunning cottage in central Helmsley with parking

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
2 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Rievaulx, near Helmsley, vacation rental in Helmsley

2 bedroom accommodation in Rievaulx, near Helmsley

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Host & Stay | Willow Cottage, vacation rental in Helmsley
Host & Stay | Willow Cottage, vacation rental in Helmsley
Host & Stay | Willow Cottage, vacation rental in Helmsley

Host & Stay | Willow Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Showing results 1-50 of 72