Discover the Top Six Holiday Cottages for Two in Skipton

When it comes to planning a holiday for two in Skipton, a charming market town in North Yorkshire, finding the perfect holiday cottage is crucial. The serene countryside, historic charm, and a plethora of activities make Skipton an ideal destination for couples looking to escape the hustle and bustle of daily life. In this comprehensive guide, we’ve handpicked six enchanting holiday cottages tailored for two people. Say goodbye to the endless scrolling on, Airbnb, VRBO, and Holiday Lettings, as we bring you the cream of the crop, all in one place.

All the cottages in this Guide are dog friendly.

Thisledo Holiday Cottage


Nestled in the heart of the breathtaking Yorkshire Dales, Skipton welcomes you to Thisledo Holiday Cottage – a charming, dog-friendly escape perfect for travelers seeking the perfect balance of modern comfort and traditional charm. Discover the tranquil beauty of the surrounding countryside and the historic town of Skipton while enjoying a cosy, pet-friendly retreat.

Cottage Overview:

Thisledo Holiday Cottage is a traditional stone cottage that combines the allure of history with the convenience of modern living. As you step inside, you’ll be greeted by a warm and welcoming interior, thoughtfully decorated and furnished to ensure your utmost comfort.

  • Fully Equipped Kitchen: The well-equipped kitchen is a haven for those who love to cook. Prepare delicious meals or simply brew your morning coffee to enjoy on the charming bistro table and chairs in the rear flagged area.
  • Cosy Living Room: The living room beckons with an open gas fire, creating a snug atmosphere where you can unwind after a day of exploration. Curl up on the comfortable sofa with your four-legged friend or enjoy the 42″ Smart TV, offering access to streaming services like Netflix and Amazon Prime.
  • Peaceful Bedroom: The good-sized bedroom boasts a comfortable double bed, promising a restful night’s sleep after your adventures in the Dales.
  • Invigorating Shower: The spacious bathroom features an invigorating shower, leaving you feeling refreshed and revitalized.

Dog-Friendly Amenities:

Thisledo Holiday Cottage is more than just dog-friendly; it’s a true canine haven. Located in a quiet and peaceful part of Skipton town center, close to Aireville Park, the cottage offers easy access to beautiful walking routes where your furry companion can roam to their heart’s content.

Convenient Stay:

  • Enjoy the convenience of ample street parking just a few minutes’ walk from the cottage.
  • Short stay parking is available right in front of the cottage for easy loading and unloading on arrival and departure days.
  • Access a digital guest welcome book to enhance your stay.
  • Stay connected with free WIFI via fiber broadband.

Exploring Skipton:

Skipton is a historic market town with an array of shops, cafes, and restaurants to explore. A must-see attraction is the famous Skipton Castle, which is not only a historical gem but is also dog-friendly, ensuring that your furry friend can join you on this fascinating journey into the past.

Book Your Stay:

Thisledo Holiday Cottage offers the perfect home base for exploring the enchanting Yorkshire Dales with your four-legged companion. Whether you’re seeking relaxation, adventure, or a bit of both, our cosy cottage welcomes you with open arms. Book your stay today and immerse yourself in the beauty of Skipton and the Yorkshire Dales with your loyal furry friend by your side. We can’t wait to welcome you to our delightful cottage!

The Bailey Cottage – Skipton

Nestled in the heart of the picturesque town of Skipton, The Bailey Cottage offers a cosy and charming retreat for your Yorkshire getaway. This delightful holiday cottage is ideally located just a mere 2-minute walk from Skipton’s cobbled high street, making it the perfect base for exploring this historic market town and the surrounding beauty of the Yorkshire Dales.


  • Accommodation All on One Level
  • First Floor:
    • 12 steps to entrance.
    • Living/Dining Room: Cosy ambiance with a multi-fuel stove and Sky TV (entertainment package).
    • Kitchen: Fully equipped with an electric hob, electric oven, microwave, fridge, slimline dishwasher, and washing machine.
    • Bedroom: A comfortable kingsize bed awaits you for a restful night’s sleep.
    • Bathroom: Features a shower over the bath and toilet.
  • Gas central heating, electricity, bed linen, towels, and Wi-Fi are all included.
  • An initial supply of logs for the wood burner is provided.
  • Access to a shared garden with garden furniture for enjoying the outdoors.
  • Private parking space for one car.
  • This is a non-smoking property.

Location: The Bailey Cottage is located within the conservation area of Skipton and offers captivating views overlooking the bailey towards the historic castle grounds. With a short stroll, you’ll find yourself on Skipton’s charming cobbled high street, where you can explore local shops, cafes, and restaurants. This central location is perfect for those looking to immerse themselves in the town’s rich history and vibrant atmosphere.

Book Your Stay: For bookings and availability, you can visit the property listing on Plan your escape to The Bailey Cottage and experience the warm, welcoming ambiance of this charming retreat.

Additional Services:

  • Enjoy the shared garden with the owner’s dogs, Poppy and Joe, in good weather.
  • Bikes are available for hire, allowing you to explore the beautiful Yorkshire countryside.
  • For a touch of luxury, consider arranging chauffeur-driven tours of the nearby Dales in a classic 1949 Bentley Mk VI. This unique experience includes a delightful pub lunch and can be tailored to your preferences. Costs and itineraries are flexible based on your requirements, ensuring an unforgettable adventure during your stay.

Discover the beauty of Skipton and the Yorkshire Dales with The Bailey Cottage as your home away from home.

Craven Cottage – Skipton

Nestled near the historic Skipton Castle, Craven Cottage offers a delightful and cosy holiday retreat, perfect for exploring the charming town and its surroundings. This Grade II listed cottage boasts a unique character and is set in a quiet backwater near the Leeds and Liverpool Canal, making it an ideal base for your exploration of the town and its beautiful surroundings.


  • Ground Floor:
    • Living/Dining Room: Featuring a wood burner for those cosy nights in, and a Smart TV for entertainment.
    • Kitchen: Equipped with an electric cooker, microwave, and freezer for your convenience.
  • First Floor:
    • Bedroom: A comfortable double bed awaits you for a peaceful night’s sleep.
    • Bathroom: Complete with a shower over the bath and toilet.


  • Gas central heating, electricity, bed linen, towels, and Wi-Fi are included.
  • Cot and highchair are available for families.
  • The enclosed patio offers garden furniture for enjoying the outdoors.
  • Private parking space for one car.
  • This is a non-smoking property.

Location: Craven Cottage enjoys a prime location, just 440 yards from the iconic Skipton Castle. The town’s cobbled high street, adorned with vibrant markets, is within walking distance. The Leeds and Liverpool Canal, with its colorful narrow boats, provides an idyllic backdrop for leisurely walks. Skipton, known as “The Gateway to The Dales,” offers the perfect starting point for exploring the beauty of the Yorkshire Dales National Park.

Exploration Beyond:

  • Nearby, the picturesque village of Embsay (2 miles) boasts its very own steam railway, a treat for railway enthusiasts of all ages.
  • The historic market town of Settle (17 miles) is easily accessible, offering a variety of shops, pubs, and restaurants to explore.

Book Your Stay: For bookings and availability, please visit the property listing on the provided platform. Craven Cottage promises a unique and charming stay, with its historical significance and excellent location for discovering the beauty of Skipton and the Yorkshire Dales.

Additional Information: Shop at a convenient 100 yards away, while a pub and restaurant are just 200 yards from the cottage.

Plan your escape to Craven Cottage and experience a blend of history, comfort, and natural beauty in the heart of Skipton.

Town Cottage

Are you dreaming of a romantic escape in the picturesque town of Skipton, nestled in the heart of the Yorkshire Dales? Look no further! Town Cottage, a delightful stone-built terraced cottage, offers a cosy and characterful haven for you and your loved one. Let’s take a closer look at this enchanting retreat that promises a perfect getaway.

Intimate Elegance

Town Cottage spans two floors, providing ample space for a romantic stay. The king-size bedroom, adorned with a sleigh bed, exudes warmth and comfort, setting the stage for a peaceful night’s sleep. The contemporary bathroom offers a choice between a relaxing bubble bath or an invigorating shower.

Homely Comfort

This charming retreat boasts a well-equipped kitchen, making it easy to whip up a delicious home-cooked meal. The living and dining room, featuring a gas fire and a log burner, creates a romantic ambiance for evenings in. Curl up on the sofa and enjoy your favorite movies on the new smart TV with FreeSat, or challenge each other to a board game.

Convenient Amenities

Town Cottage ensures your stay is hassle-free. Gas central heating keeps you warm, and you’ll find a gas hob, combi microwave/oven, fridge, freezer, and a washing machine at your disposal. Bed linen and towels are included in the rent, and there’s off-road parking for one car.

Pet-Friendly Retreat

If you’re a dog owner, Town Cottage welcomes one well-behaved dog to join you on your romantic adventure.

Local Exploration

Skipton town center, just a stone’s throw away, offers a vibrant selection of restaurants, tea rooms, and coffee shops for dining out. Don’t forget to explore the traditional market, which sells fresh produce throughout the year, including local cheeses, fish, meats, and fresh vegetables.

Known as The Gateway to the Dales, Skipton boasts a medieval castle, canal boat trips, swimming pools, golf courses, excellent cycling routes, tennis courts, and an array of walks, ranging from easy rambles to challenging fell hikes.

Explore the Surroundings

Venture beyond Skipton to discover the beauty of the Yorkshire Dales National Park. Visit charming villages like Gargrave, Malham, Settle, and Kettlewell, each with its unique charm and attractions. Don’t miss the Embsay & Bolton Abbey Steam Railway or the Settle to Carlisle railway for a historic journey through breathtaking landscapes.


Town Cottage is your ideal retreat in Skipton, offering a blend of modern comfort and historic charm. Whether you’re planning a romantic weekend getaway or an extended stay, this cottage has everything you need for an unforgettable experience. Book your stay today and create beautiful memories in the heart of the Yorkshire Dales. Don’t miss the chance to experience Skipton’s beauty and the warmth of Town Cottage, an inviting and romantic escape at any time of the year.

Journeyman Loft


Nestled in the heart of Skipton, the picturesque “Journeyman Loft” cottage offers a unique and welcoming retreat for those seeking a romantic escape or a peaceful getaway. With commanding views over the town towards the church, castle, Skipton woods, and the surrounding fells, this end-terrace cottage promises a stay filled with comfort and charm. Let’s explore the features and attractions that make this cottage a gem in Skipton.

Cosy Living Spaces

This spacious cottage spans three levels, ensuring that you have plenty of room to unwind. The spacious bedroom offers a super king-size double bed, which can be converted into twin beds upon request, providing the flexibility to accommodate your specific needs. The bathroom features a hip bath and a shower over, basin, and WC.

The open-plan living and dining area is split-level and includes a galleried kitchen, accessible via a few steps from the sitting/dining area. The cottage offers modern amenities, including an electric oven and hob, microwave, fridge/freezer, dishwasher, washer/dryer, and a tumble dryer in the garage.

Woodburning Stove and Spectacular Views

The heart of the cottage is the sitting area, which features a woodburning stove, creating a cosy atmosphere perfect for those romantic evenings in. From this vantage point, you can take in the views over Skipton, which include the church, castle, woods, and the breathtaking surrounding fells. You’ll also find a TV with Freeview and WiFi, allowing you to stay connected and entertained during your stay.

Convenience and Comfort

Your comfort is a priority here. The cottage provides bed linen and towels and is equipped with gas central heating throughout, ensuring that you stay warm and comfortable. A starter pack for the woodburning stove is provided, with additional wood available on-site on an honesty box basis.

Pet-Friendly and No Smoking

For those traveling with furry companions, one well-behaved dog is welcome, with the option to request an additional dog. However, please note that no other pets are accepted. Smoking is also not allowed in the cottage.

Exploring Skipton

Skipton is known as “The Gateway to the Dales” and offers a variety of attractions for visitors. The historic Skipton Castle, one of Britain’s finest medieval castles, is a must-see. You can also enjoy boat trips from the historic canal basin. Skipton boasts numerous shops, restaurants, and tea rooms, as well as a traditional market selling fresh produce.

Outdoor Adventures

Close to the cottage, you’ll find excellent cycling routes and a range of walks, from easy rambles to challenging fell hikes. The surrounding natural beauty is a paradise for outdoor enthusiasts.


“Journeyman Loft” is more than just a cottage; it’s an invitation to discover the charm and beauty of Skipton. Whether you’re seeking a romantic retreat or a peaceful escape, this cottage’s unique layout, modern amenities, and unbeatable views make it the perfect choice. Book your stay today and experience Skipton’s splendor from the comfort of this enchanting cottage. Please note that this property is suitable for babes-in-arms and children over 12.

Skipton is a hidden gem for couples seeking a tranquil retreat. The holiday cottages mentioned above provide the perfect escape from the everyday hustle and bustle with your four legged friend, allowing you to unwind and enjoy quality time together. By exploring this curated list of cottages, you’ll avoid the overwhelm of sifting through countless options on various booking platforms and cottage agencies websites. Book your dream getaway in Skipton today and create beautiful memories in one of these enchanting cottages!

Skipton Web design by 418Design Ltd

Copyright 2024. All Rights Reserved