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 Vacation Rentals

List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 mi
76 rentals in Helmsley.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
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
More info
Check in
Check out

2 bedroom accommodation in Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Helmsley, vacation rental in Helmsley

2 bedroom accommodation in Helmsley

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

1 bedroom accommodation in Nawton, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Nawton, near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Nawton, near Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Nawton, near Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

A Delightful Stone Cottage Located in the North York Moors National Park., vacation rental in Helmsley
A Delightful Stone Cottage Located in the North York Moors National Park., vacation rental in Helmsley
A Delightful Stone Cottage Located in the North York Moors National Park., vacation rental in Helmsley

A Delightful Stone Cottage Located in the North York Moors National Park.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

Save time - get the best Helmsley rentals sent straight to your email!
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
More info
Vrbo.com logo
Check in
Check out

Self Catering 3 Bedroom, vacation rental in Helmsley
Self Catering 3 Bedroom, vacation rental in Helmsley
Self Catering 3 Bedroom, vacation rental in Helmsley

Self Catering 3 Bedroom

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection

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
More info
Vrbo.com logo
Check in
Check out

1 bedroom accommodation in Rievaulx near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Rievaulx near Helmsley, vacation rental in Helmsley
1 bedroom accommodation in Rievaulx near Helmsley, vacation rental in Helmsley

1 bedroom accommodation in Rievaulx near Helmsley

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

3 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley
3 bedroom accommodation in Bilsdale, near Helmsley, vacation rental in Helmsley

3 bedroom accommodation in Bilsdale, near Helmsley

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

2 bedroom accommodation in Nawton, near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Nawton, near Helmsley, vacation rental in Helmsley
2 bedroom accommodation in Nawton, near Helmsley, vacation rental in Helmsley

2 bedroom accommodation in Nawton, near Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out

4 bedroom accommodation in Helmsley, vacation rental in Helmsley
4 bedroom accommodation in Helmsley, vacation rental in Helmsley
4 bedroom accommodation in Helmsley, vacation rental in Helmsley

4 bedroom accommodation in Helmsley

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out

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
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

Pinfold Cottage - Three Bedroom House, Sleeps 6, vacation rental in Helmsley
Pinfold Cottage - Three Bedroom House, Sleeps 6, vacation rental in Helmsley
Pinfold Cottage - Three Bedroom House, Sleeps 6, vacation rental in Helmsley

Pinfold Cottage - Three Bedroom House, Sleeps 6

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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 4
Match: Sleeps
More info
Check in
Check out

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
More info
Check in
Check out

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
More info
Check in
Check out
Payment Protection

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
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

Ivy Cottage, HELMSLEY, vacation rental in Helmsley
Ivy Cottage, HELMSLEY, vacation rental in Helmsley
Ivy Cottage, HELMSLEY, vacation rental in Helmsley

Ivy Cottage, HELMSLEY

Rental Home
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Bellwether, HELMSLEY, vacation rental in Helmsley
Bellwether, HELMSLEY, vacation rental in Helmsley
Bellwether, HELMSLEY, vacation rental in Helmsley

Bellwether, HELMSLEY

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Host & Stay | Buckingham Square, vacation rental in Helmsley
Host & Stay | Buckingham Square, vacation rental in Helmsley
Host & Stay | Buckingham Square, vacation rental in Helmsley

Host & Stay | Buckingham Square

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

Host & Stay | Buckingham Square, vacation rental in Helmsley
Host & Stay | Buckingham Square, vacation rental in Helmsley
Host & Stay | Buckingham Square, vacation rental in Helmsley

Host & Stay | Buckingham Square

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection

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
More info
Check in
Check out
Payment Protection

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
More info
Check in
Check out
Payment Protection

Gardener's Cottage Nawton, vacation rental in Helmsley
Gardener's Cottage Nawton, vacation rental in Helmsley
Gardener's Cottage Nawton, vacation rental in Helmsley

Gardener's Cottage Nawton

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection

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
More info
Check in
Check out

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
More info
Check in
Check out
Payment Protection

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
More info
Check in
Check out
Payment Protection

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
More info
Check in
Check out

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
More info
Check in
Check out

THE BRYE, pet-friendly, WiFi, near Thirsk, vacation rental in Helmsley
THE BRYE, pet-friendly, WiFi, near Thirsk, vacation rental in Helmsley
THE BRYE, pet-friendly, WiFi, near Thirsk, vacation rental in Helmsley

THE BRYE, pet-friendly, WiFi, near Thirsk

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out

Shippon, Beadlam, vacation rental in Helmsley
Shippon, Beadlam, vacation rental in Helmsley
Shippon, Beadlam, vacation rental in Helmsley

Shippon, Beadlam

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out

Rednal Cottage, Helmsley, vacation rental in Helmsley
Rednal Cottage, Helmsley, vacation rental in Helmsley
Rednal Cottage, Helmsley, vacation rental in Helmsley

Rednal Cottage, Helmsley

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out

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
More info
Check in
Check out

The Bothy, vacation rental in Helmsley
The Bothy, vacation rental in Helmsley
The Bothy, vacation rental in Helmsley

The Bothy

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

THE COTTAGE, WiFi, open-plan, near Thirsk, vacation rental in Helmsley
THE COTTAGE, WiFi, open-plan, near Thirsk, vacation rental in Helmsley
THE COTTAGE, WiFi, open-plan, near Thirsk, vacation rental in Helmsley

THE COTTAGE, WiFi, open-plan, near Thirsk

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out

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
More info
Check in
Check out

Castle View, HELMSLEY, vacation rental in Helmsley
Castle View, HELMSLEY, vacation rental in Helmsley
Castle View, HELMSLEY, vacation rental in Helmsley

Castle View, HELMSLEY

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

PreviousNext
12
Frequently Asked Questions about Helmsley

Yes, here are some popular vacation rentals in Helmsley that have a pool:See all vacation rentals with a pool in Helmsley on Tripadvisor

Yes, here are some popular vacation rentals in Helmsley that have internet access:See all vacation rentals in Helmsley on Tripadvisor