Skip to main content

Self-Catering Cottages in Helmsley

63 holiday cottages to rent

Photo © Paul Coggins, Google Maps

The Helmsley Retreat from £817

North Yorkshire · 0.1 miles away

The Helmsley Retreat

Two-bedroom cottage in Helmsley with hot tub and sauna in private garden; one dog welcome.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Cliff House from £466

North Yorkshire · 0.1 miles away

Cliff House

Cottage in Helmsley, North Yorkshire sleeping six guests in three bedrooms.

🛏️ 3 beds 👥 Sleeps 6
Cottage
29 Bondgate from £552

North Yorkshire · 0.1 miles away

29 Bondgate

29 Bondgate is a characterful cottage settled in Helmsley, in North Yorkshire and can sleep four people in two bedrooms.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Cottage
Holly-Garth from £807

North Yorkshire · 0.1 miles away

Holly-Garth

Holly-Garth, North Yorkshire: four-bedroom house with two sitting rooms, three bathrooms, and everything included from linen to Wi-Fi.

🛏️ 4 beds 👥 Sleeps 8 🐾 Pets welcome
Cottage
The Cart House from £998

North Yorkshire · 0.1 miles away

The Cart House

The Cart House, Helmsley: three-bedroom stone house with enclosed garden, one dog welcome, near Arts Centre.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Cottage
8 Pottergate Mews from £517

North Yorkshire · 0.2 miles away

8 Pottergate Mews

This mid-terrace cottage is in the market town of Helmsley near to Kirkbymoorside and can sleep four people in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Lily Pad from £537

North Yorkshire · 0.2 miles away

Lily Pad

Two-bedroom cottage in Helmsley market town, walking distance from independent shops, pubs and the castle.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Ryegate Cottage from £591

North Yorkshire · 0.2 miles away

Ryegate Cottage

Two-bedroom cottage in Helmsley, North Yorkshire, with a working kitchen and garden ideal for exploring the market town and surrounding countryside.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
The Nest from £313

North Yorkshire · 0.2 miles away

The Nest

One-bedroom apartment in Helmsley town centre, 50 metres from the market place, with parking and garden access.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Cottage
Ridings Cottage from £1,266

North Yorkshire · 0.2 miles away

Ridings Cottage

Three-bedroom cottage in Helmsley with a wood burner, each bedroom has its own bathroom, and private parking in a gated courtyard.

🛏️ 3 beds 👥 Sleeps 6
Cottage
Toad Hall from £677

North Yorkshire · 0.2 miles away

Toad Hall

Grade II listed cottage in Helmsley town centre, 2 bedrooms, 2 bathrooms, sleeping 4, with enclosed garden and parking.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Rye Cottage from £831

North Yorkshire · 0.2 miles away

Rye Cottage

Three-bedroom cottage in Helmsley town centre, sleeping 6, with a wood burner and enclosed garden.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Ivy Cottage from £449

North Yorkshire · 0.2 miles away

Ivy Cottage

This end-terrace cottage is located in Helmsley and can sleep five people in three bedrooms.

🛏️ 3 beds 👥 Sleeps 5
Cottage
Bridge House from £417

North Yorkshire · 0.3 miles away

Bridge House

Grade II listed house in Helmsley with 2 bedrooms, 3 bathrooms, garden to the River Rye, and parking.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Popleys from £727

North Yorkshire · 0.3 miles away

Popleys

Three-bedroom cottage in Helmsley, North Yorkshire, minutes from the market town centre and North York Moors National Park.

🛏️ 3 beds 👥 Sleeps 4
Cottage
The Garth from £547

North Yorkshire · 0.3 miles away

The Garth

The Garth, Helmsley, North Yorkshire: three-bedroom cottage with open-plan ground floor and direct patio access.

🛏️ 3 beds 👥 Sleeps 5 🐾 Pets welcome
Cottage
Rosebeck from £867

North Yorkshire · 0.4 miles away

Rosebeck

Two-bedroom cottage in Helmsley with garden, patio and detached sun room; one dog welcome.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Borough Beck Cottage from £557

North Yorkshire · 0.4 miles away

Borough Beck Cottage

Borough Beck Cottage, Helmsley: three-bedroom cottage with full kitchen, woodburner and enclosed garden with patios.

🛏️ 3 beds 👥 Sleeps 5 🐾 Pets welcome
Cottage
Lawns Cottage from £453

North Yorkshire · 1.5 miles away

Lawns Cottage

Stone cottage sleeping 4 in North Yorkshire village, with one pet welcome and a large garden for outdoor space.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Peg's Cottage from £288

North Yorkshire · 1.8 miles away

Peg's Cottage

This charming, detached stone cottage, set in a hamlet close to the North Yorkshire market town of Helmsley, can sleep two people in one double bedroom.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Cottage
Shippon from £371

North Yorkshire · 2.1 miles away

Shippon

Shippon rests just outside Beadlam, North Yorkshire sleeping two in one bedroom.

🛏️ 1 bed 👥 Sleeps 2
Griff Lodge from £454

North Yorkshire · 2.1 miles away

Griff Lodge

This detached bungalow rests in the village of Harome in North Yorkshire and can sleep four people in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Bellwether from £263

North Yorkshire · 2.1 miles away

Bellwether

A detached shepherd’s hut situated on the outskirts of the market town of Helmsley, sleeping up to two people, in one bedroom.

🛏️ 1 bed 👥 Sleeps 2
Cottage
Foxglove Cottage from £510

North Yorkshire · 2.2 miles away

Foxglove Cottage

This ground-floor cottage rests in Harome near Beadlam, North Yorkshire and can sleep two people in one bedroom.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Holly Cottage from £662

North Yorkshire · 2.3 miles away

Holly Cottage

Holly Cottage in Harome near Beadlam, sleeps six people in three bedrooms.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Auburn House from £596

North Yorkshire · 2.3 miles away

Auburn House

A beautiful detached period property in the village of Beadlam near Helmsley and can sleep 8 people in four bedrooms.

🛏️ 4 beds 👥 Sleeps 8
Angel Cottage from £437

North Yorkshire · 2.4 miles away

Angel Cottage

Two-bedroom detached cottage near Oswaldkirk, within reach of the North York Moors, with accessible ground-floor layout.

🛏️ 2 beds 👥 Sleeps 5
Silent Springs from £453

North Yorkshire · 2.5 miles away

Silent Springs

One-bedroom cottage near York with fully equipped kitchen, smart TV, and enclosed garden; one dog welcome.

🛏️ 1 bed 👥 Sleeps 4 🐾 Pets welcome
Walnut Cottage from £282

North Yorkshire · 2.5 miles away

Walnut Cottage

Walnut Cottage near Helmsley, North Yorkshire, sleeps two guests in one bedroom.

🛏️ 1 bed 👥 Sleeps 2
Cottage
Highfield Barn from £407

North Yorkshire · 2.5 miles away

Highfield Barn

Detached barn conversion for two in North Yorkshire, fully equipped with heating, wifi and woodburner.

🛏️ 1 bed 👥 Sleeps 2
Cottage
Swiss Cottage from £517

North Yorkshire · 2.6 miles away

Swiss Cottage

Detached thatched cottage near Rievaulx Abbey in North Yorkshire, sleeping 4 with views over the ruins.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Mill Cottage from £591

North Yorkshire · 2.6 miles away

Mill Cottage

Three-bedroom detached cottage near York with views of Rievaulx Abbey ruins and an open fire.

🛏️ 3 beds 👥 Sleeps 5 🐾 Pets welcome
Cottage
Mill House from £543

North Yorkshire · 2.6 miles away

Mill House

Mill House, North Yorkshire: Grade II listed cottage beside Rievaulx Abbey ruins with an open fire and enclosed garden.

🛏️ 3 beds 👥 Sleeps 5 🐾 Pets welcome
Cottage
3 Valley View Lodges from £322

North Yorkshire · 2.7 miles away

3 Valley View Lodges

This detached lodge rests in Nawton near Helmsley, North Yorkshire and can sleep four people in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Ash Lodge from £413

North Yorkshire · 2.7 miles away

Ash Lodge

Detached single-storey lodge for four in North Yorkshire, between Helmsley and Kirkbymoorside, with Castle Howard and Duncombe Park within easy reach.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Robin Lodge from £367

North Yorkshire · 2.7 miles away

Robin Lodge

Single-storey lodge with two bedrooms near Helmsley, North Yorkshire, on a quiet site with countryside views.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Wren Lodge from £393

North Yorkshire · 2.7 miles away

Wren Lodge

Two-bedroom North Yorkshire lodge on single-storey layout with country views, near Helmsley and Rievaulx Abbey.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Ashberry Retreats - Ashberry Farm Cottage from £333

North Yorkshire · 2.8 miles away

Ashberry Retreats - Ashberry Farm Cottage

One-bedroom cottage on a working farm in North Yorkshire, overlooking the duck pond with garden access.

🛏️ 1 bed 👥 Sleeps 3
Cottage
Low Grounds Cottage from £493

North Yorkshire · 2.9 miles away

Low Grounds Cottage

Low Grounds Cottage by Harome, Yorkshire sleeps four in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
St Gregory’s Cottage from £356

North Yorkshire · 3.1 miles away

St Gregory’s Cottage

St Gregory’s Cottage in Oswaldkirk, sleeps two people in one bedroom.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Honeysuckle Cottage from £386

North Yorkshire · 3.1 miles away

Honeysuckle Cottage

Honeysuckle Cottage in Oswaldkirk, Yorkshire sleeps four people in two bedrooms

🛏️ 2 beds 👥 Sleeps 4
Cottage
Pheasant Lodge

North Yorkshire · 3.1 miles away

Pheasant Lodge

Two-bedroom luxury lodge near Helmsley in North Yorkshire, with countryside views from decking and direct access to the North York Moors.

🛏️ 2 beds 👥 Sleeps 4
Isca Lodge - With Decking from £801

North Yorkshire · 3.1 miles away

Isca Lodge - With Decking

Isca Lodge – with Decking near Wombleton, North Yorkshire, sleeps 6 in 3 rooms.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Summerfield Farm Cottage from £255

North Yorkshire · 3.3 miles away

Summerfield Farm Cottage

This semi-detached cottage rests near Helmsley and can sleep four people in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Lilac Cottage from £292

North Yorkshire · 3.3 miles away

Lilac Cottage

Lilac Cottage in Wombleton, North Yorkshire, sleeps four guests in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Leysthorpe Grange - Crayke Cottage from £691

North Yorkshire · 3.4 miles away

Leysthorpe Grange - Crayke Cottage

Two-bedroom cottage near Helmsley with underfloor heating, woodburner and garden views across North Yorkshire countryside.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Leysthorpe Grange - Coach House from £697

North Yorkshire · 3.4 miles away

Leysthorpe Grange - Coach House

Two-bedroom coach house in North Yorkshire with underfloor heating, woodburning stove, and one pet stays free.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Leysthorpe Grange - The Carriage House from £1,202

North Yorkshire · 3.4 miles away

Leysthorpe Grange - The Carriage House

The Carriage House, Leysthorpe: four-bedroom North Yorkshire farmhouse with full heating, Wi-Fi and parking included.

🛏️ 4 beds 👥 Sleeps 8 🐾 Pets welcome
Cottage
St. Anthonys from £493

North Yorkshire · 3.7 miles away

St. Anthonys

Three-bedroom cottage in Ampleforth village, North Yorkshire, sleeping five, with a garden and pub nearby.

🛏️ 3 beds 👥 Sleeps 5 🐾 Pets welcome
Cottage
The Old Post Office from £897

North Yorkshire · 3.9 miles away

The Old Post Office

The Old Post Office in Ampleforth, North Yorkshire, sleeps ten in five bedrooms.

🛏️ 5 beds 👥 Sleeps 10
Ford End Cottage from £536

North Yorkshire · 4 miles away

Ford End Cottage

This converted carriage shed rests in Ampleforth, North Yorkshire and can sleep six people in three bedrooms.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Cottage
Mole End from £314

North Yorkshire · 4 miles away

Mole End

Mole End near Helmsley, North Yorkshire and sleeps two people in one bedroom.

🛏️ 1 bed 👥 Sleeps 2
Cottage
The Burrows from £464

North Yorkshire · 4 miles away

The Burrows

The Burrows rests near Helmsley and can sleep five people in three bedrooms.

🛏️ 3 beds 👥 Sleeps 5
Cottage
Temple Hill View from £519

North Yorkshire · 4.1 miles away

Temple Hill View

Temple Hill View in Ampleforth, North Yorkshire, sleeps six guests.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Cottage
6 Fairfax Close from £442

North Yorkshire · 4.1 miles away

6 Fairfax Close

6 Fairfax Close rests in Ampleforth, and can sleep four people in two bedrooms.

🛏️ 2 beds 👥 Sleeps 4
Pear Tree Cottage from £523

North Yorkshire · 4.2 miles away

Pear Tree Cottage

One-bedroom cottage in a converted farm building near York, with parking and an enclosed garden where one pet stays free.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Cottage
Plum Tree Cottage from £577

North Yorkshire · 4.2 miles away

Plum Tree Cottage

One-bedroom cottage in North Yorkshire with free pet stay, on-site parking and garden.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Cottage
Ash Tree Cottage from £423

North Yorkshire · 4.2 miles away

Ash Tree Cottage

Two-bedroom ground-floor cottage in North Yorkshire farmland with direct access to walking routes; one dog stays free.

🛏️ 2 beds 👥 Sleeps 3 🐾 Pets welcome
Cottage
Elm Tree Cottage from £627

North Yorkshire · 4.2 miles away

Elm Tree Cottage

Two-bedroom converted barn cottage in North Yorkshire, near Kirkbymoorside, with one dog welcome and direct farmland access.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Oak Tree Cottage from £661

North Yorkshire · 4.2 miles away

Oak Tree Cottage

Two-bedroom converted farm cottage near York with countryside views, walking and cycling on the doorstep.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
The Nab from £417

North Yorkshire · 4.4 miles away

The Nab

The Nab, North Yorkshire glamping lodge for four with hot tub, near Helmsley and the North York Moors.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Ristbrow Farm from £1,862

North Yorkshire · 4.5 miles away

Ristbrow Farm

Grade II listed 18th-century farmhouse near Hawnby with six bedrooms, hot tub, and games room; sleeps 12.

🛏️ 6 beds 👥 Sleeps 12 🐾 Pets welcome
Feather Holme Farm Cottage from £387

North Yorkshire · 5 miles away

Feather Holme Farm Cottage

Two-bedroom cottage on a working farm near Helmsley, with views over Bilsdale woodland and direct access to walking routes.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome

More cottages and stays in Helmsley

Hotels, B&Bs, cottages and apartments on Booking.com, with live prices and availability.

🏡

Know a cottage in Helmsley that's missing?

Run one yourself or know a good one? Suggest it and we'll review it for the site. Listings are free.

Add a cottage

Get the best UK staycation deals

The latest offers on cottages, campsites and hotels, plus new ideas for breaks around Britain. Straight to your inbox, no spam.

By signing up you agree to receive emails from Staycation.co.uk. Unsubscribe any time. See our Privacy Policy.