Family-friendly vacation rentals in Helmsley

Central Fully Ensuite house sleeps 6 dog friendly

The house is in the Centre of Helmsley but located in a very quiet area with great views, close to the shops, galleries, restaurants and Duncombe Park. It is a lovely spacious house, that has 3 ensuite bathrooms and therefore is great for couples, families and small groups. It is ideal for exploring North Yorkshire. The adjacent property, 2 Stonegarth can be let with this property. It is ideal for two families that want privacy but can come together for meals etc. Well behaved dogs allowed.

Indoor spaces · Kitchen · Parking

Pretty Yorkshire Stone Cottage Harome

A charming stone cottage situated in the picturesque village of Harome, 3 miles from the market town of Helmsley.This characterful cottage is up to date with everything you need without losing original features of beamed ceilings & a cosy log burner. The cottage offers luxe accommodation with a spacious kitchen, two delightful bedrooms, a power shower, bath, well equipped kitchen & hotel grade linen. A cosy sitting room with open plan dining area. There is a little garden outside with a table.

Indoor spaces · Kitchen · Bathroom

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

Indoor spaces · Kitchen · Beach

Gorgeous country cottage, Nawton near Helmsley

A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.

Family · Kitchen · Checkout

*The Vicarage Annexe, Carlton, North Yorks 1BR S/C

The Vicarage Annexe is a beautiful, one double-bedroom facility situated at the foot of the Cleveland Hills. The building was originally built as a prayer and study room for the Vicarage. This is now a self-contained living area with en-suite facilities. The Annexe is located in the picturesque village of Carlton-in-Cleveland, which is in the North Yorkshire Moors National Park and this is an ideal location for a couple who enjoy the countryside for relaxing, sightseeing, walking or cycling.

Family · Indoor spaces · Walkability

York Poetree House, tiny treehouse home for one

Reconnect and wake up into nature at this unforgettable escape. Secluded treehouse with everything you need to soothe and inspire. Self cater, arrange meals provided by your host (a professional chef), or try one of the many eateries in town. Shops nearby. Your own private bathroom is situated a few yards away in the main house. You also can enjoy our beautiful garden, lily pond and friendly cat, Nina. Your hosts are always on hand to ensure a comfortable and nourishing experience.

Family · Kitchen · View

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annexe is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annexe dates back to the 16th century and is full of charm. You can walk from our Annexe straight up onto the Cleveland way where you can walk or bike for miles. Our Annexe is a popular stop off for people walking the coast to coast. We are also very close to some great pubs and restaurants.

Family · Kitchen · Access

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set on a horse stud farm surrounded by 220 acres with stunning countryside views you’re sure to feel relaxed from the minute you arrive. Cecil cottage sleeps up to 5 guests and has a fully equipped kitchen, modern bathroom which has a shower/bath located downstairs. There is also a wood burner and an enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.

Indoor spaces · Family · Value

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.

Kitchen · Indoor spaces · Checkout

The Flat @ 2 Castlegate

Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

Family · Kitchen · Decor

Clothes Prop Cottage, a Helmsley hideaway

Clothes Prop Cottage is located in the heart of Helmsley, just a couple of minutes walk from the shops, tea rooms, pubs and restaurants in this beautiful North Yorkshire market town. The property is available for 3 night weekend and 4 night mid week stays as well as full 7 night breaks. The property suits couples looking for a relaxing stay in the Yorkshire countryside, with their beloved pets welcome!

Family · Kitchen · Parking

Boutique log cabin with spectacular moorland views

Commanding panoramic views over Newton Dale and the North York Moors Steam Railway, High Kingthorpe Lodge is a boutique-style holiday retreat set in two and a half acres of private woodland. This lovely lodge and its stunning location are a haven of comfort and tranquility and yet only a short trip away from some of North Yorkshire's most popular attractions.

Kitchen · Family · Cleanliness