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Pickering Luxury Rentals

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    Travelers to Pickering are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    17 Matching Rentals in PickeringView all 117 rentals
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    No 2 The Ropery1 / 21
    (70)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    The Barn at Rigg End Pickering1 / 16
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    North York Moors National Park - dog friendly1 / 11
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated in the heart of the vibrant market town of Pickering, discover all that the North York Moors has to offer from this charming property. Situated in the heart of the vibrant market town of Pickering, this charming cottage has been lovingly restored with great care and attention to...
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    Location Information
    Pickering, North Yorkshire YO18 7DG
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Woodlea1 / 19
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Parking
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 2018
    We stayed here with family for 3 nights in January 2018 and had a great time. The cottage is located down a very bumpy track but this is only 200/300m long and wasnt too bad...
    Reviewed June 20, 2017
    Absolutely perfect. Stunning location, beautiful house with everything we could want. Ideal holiday. Excellent communication with the owners. We would love to go back one day...
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    About this property
    (Due to long term let cancellation from Sept 2019 for 1 year, Woodlea is now available again to rent for weeks and weekends, 10% discount for Sept & Oct) Woodlea is positioned on the hillside of one of the most picturesque valleys in the North York Moors. There are 3 pubs/restaurants within walking...
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    Pickering, North Yorkshire YO18 8SE
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pasture View Cottage - Pickering1 / 33
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Porch
    • DVD Player
    • Parking
    • Wi-Fi
    • Central Heating
    • Grill
    • Outdoor Dining Area
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2018
    Fantastic cottage and a great welcome - will definitely return.It was perfect for the two families, including 4 children.
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    About this property
    PASTURE VIEW Sleeps 8 + cot Easy walking access 4 BEDROOM single storey cottage with private garden, garden furniture and BBQ : Ground floor - Spacious sitting room with open beamed ceiling and stone fireplace with living flame gas fire and dining area/ kitchen with dishwasher &...
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    Pickering, North Yorkshire YO18 8LL
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Medds Farm House, Rosedale, North York Moors1 / 27
    (20)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2019
    A large, fully equipped house with everything you could want provided. Wonderful gardens with plenty of places to sit and enjoy the spectacular views. The wildlife around the...
    Reviewed May 15, 2019
    Proper moorland isolation but only a stone's throw from some great pubs and amenities. We have four kids and two dogs so needed some space and Medds Farm definitely has that...
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    About this property
    As featured on BBC's 'Escape to the Country' 2019, Medds Farm House is perched on the side of picturesque Rosedale in the heart of the North York Moors National Park. Medds is an ideal holiday home for your biking or walking holiday or for simply getting your family together to enjoy the peace and...
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    Pickering, North Yorkshire YO18 8SQ
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    North York Moors National park - cottage & kennels1 / 18
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Secure Parking
    • Terrace
    • Balcony
    • DVD Player
    • Grill
    • Wi-Fi
    • Central Heating
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2019
    Thoroughly enjoyed our short break here. Especial thanks to Tom for getting us out of a tricky situation, and to both Louise and Tom for their hospitality and local advice...
    Reviewed January 1, 2019
    Great location. Secluded, Quiet plenty of walks and wildlife. Will visit again. WiFi can be temperamental and phone signal not the best. Both positives
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    About this property
    WILLOWS' END COTTAGE - One of a row of 4 immaculately presented cottages linked by a cloistered passage, Willows' End is a spacious cottage with solid oak floors and feature beams throughout the ground floor. It has beautiful furnishings including comfortable sofas, a large floor rug, LCD TV and...
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    Pickering, North Yorkshire YO18 8HY
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 THE OLD METHODIST CHAPEL, family friendly, luxury holiday cottage, with a1 / 12
    (8)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 30, 2018
    Quirky and cosy, well equipped property on four levels. Two good sized fridges in the kitchen, good size freezer and washer/dryer in the boot room. Everon stove (Aga style) was...
    Reviewed September 29, 2017
    What a beautiful characterful accommodation,everything we needed and more for 6 females on a hen weekend.so warm and cosy with the cooker always on and the storage heaters.we...
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    About this property
    A wonderful, unique cottage converted from an old chapel, in the village of Rosedale Abbey, sleeping eight in four bedrooms.1 The Old Methodist Chapel is a fantastic conversion of a Victorian chapel in the heart of the North York Moors National Park. Over four floor, this property sleeps eight in...
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    Rosedale Abbey, Pickering YO18 8SA
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stables Cottage - Pickering- Gateway to York Moors1 / 23
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Shared Yard
    • Parking
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2016
    The cottages were very well equipped, clean and tidy. A little dated but serviceable. The owners were full of valuable knowledge of the area, deals for trips and were very...
    Reviewed November 9, 2015
    We had a great stay over half term with our two young children. Penny and Julian were very welcoming and really helpful with recommendations on places to visit and to where to...
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    About this property
    THE STABLES - - Sleeps 2/7 + cot -- Easy walking access 3 BEDROOM single storey cottage: Ground floor - Spacious sitting room with open beamed ceiling and stone fireplace with living flame gas fire; Dining kitchen with dishwasher; one bedroom with a king size bed; one bedroom with a double and...
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    Location Information
    Pickering, North Yorkshire YO18 8LL
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    THE LONGHOUSE:17th century, spacious, characterful, log burner, en-suites, pets1 / 34
    (63)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • Patio
    • Grill
    • DVD Player
    • Parking
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Thoroughly recommend the Longhouse for a family holiday. Lots of space, clean, well equipped and brilliant hosts. The location is good and a manageable walk gets you into town...
    Reviewed July 4, 2019
    Wonderful welcoming cottage. Everything needed and more. Cosy , Quaint, full of interesting knooks and crannys, yet so much bigger than you think. Short walk from town,and on...
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    About this property
    Dating back to 17th Century, our Grade II listed Yorkshire longhouse is located in the picturesque market town of Pickering, at the edge of the beautiful North York Moors National Park. The cottage is a fine example of a cruck-framed Yorkshire longhouse which was traditionally built to accommodate...
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    Location Information
    Pickering, North Yorkshire YO188AU
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    North York Moors National park - cottage & kennels1 / 19
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Secure Parking
    • Central Heating
    • Washer
    • Grill
    • Housekeeping Included
    • Wi-Fi
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 18, 2018
    Lovely place to stay, the cottage was extremely clean and immaculately presented. The hosts were very welcoming and very knowledgeable of the area, and the whole family was...
    Reviewed June 2, 2018
    We stayed here for 7 weeks while we were waiting for our new house to be finished.The roads from Pickering were frightening with nasty bends and potholes.The cottage had...
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    About this property
    BROCK COTTAGE - One of a row of 4 immaculately presented traditional stone cottages linked by a cloistered passage. Brock Cottage has a fully fitted and fully equipped cream painted country kitchen diner with an oak table and chairs comfortably seating four, and solid oak floors and handcrafted...
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    Location Information
    Pickering, North Yorkshire YO18 8HY
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    THE OLD POST OFFICE en-suites, Smart TV, WiFi in Rosedale Abbey Ref 9374211 / 21
    (6)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Central Heating
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 2018
    Group of us visited in May. Lovely accomodation, so spacious, clean and comfortable. Situated in a beautiful village with walks from the doorstep. An area of Yorkshire we would...
    Reviewed September 18, 2017
    Just back from a stay at the old post office. It's a great place to stay, lots of room, really nice and cosy inside and comfy bedrooms. The owner has been extremely...
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    About this property
    This terraced property is located in the North Yorkshire village of Rosedale Abbey and can sleep nine people in five bedrooms.The Old Post Office is a terraced cottage in the delightful North Yorkshire village of Rosedale Abbey. The cottage sleeps nine people and has two double bedrooms each with...
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    Rosedale Abbey, Pickering YO18 8SA
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    Eden House Holiday Cottage, Pickering, North York Moors1 / 34
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 4, 2018
    The cottage was warm,cosy and welcoming which was so important for a winter stay. The furnishings were comfortable and clean .The attention to detail was excellent...the welcome...
    Reviewed October 31, 2018
    Wonderful stone built holiday cottage in the small town of Pickering. Great location for exploring the best of North Yorkshire and the cottage itself is spot on with lots of...
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    About this property
    Eden House Holiday Cottage is a traditional country cottage offering plenty of character & charm, with the benefit of having recently (2018) been fully refurbished to a very high standard. The spacious accommodation, on the ground floor, offers a lovely cosy lounge with log burning stove, for those...
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    Location Information
    Pickering, North Yorkshire YO18 7DW
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Washer
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled adjacent to our private woodland are our 'scandinavian style' Wooden Lodges. Modern, open plan living is wrapped up in a cosy and natural style influenced by the beautiful natural setting. Living You enter our woodland lodges via a covered porch in to a boot room with coat hooks and a...
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    Pickering, North Yorkshire YO18 7JX
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a fantastic location in the centre of popular Pickering,this property is surrounded by grand Georgian architecture,cosy traditional cottages,excellent restaurants,pubs and cafes. From Pickering,the iconic North York Moors Railway travels through scenic countryside to the coastal town of...
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    Location Information
    Pickering, North Yorkshire YO18 8DY
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    North York Moors national park - cottage with hot tub & kennels1 / 16
    (31)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • DVD Player
    • Washer
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2019
    Just returned from a weekend away at Meadows edge cottage with 3 friends. We received a very warm welcome from Louise and Tom who showed us around the cottage and explained how...
    Reviewed April 16, 2019
    Peaceful, quiet location. This is a superb cottage with all mod cons. Hosts Louise and Tom were brilliant, with Louise answering my many questions quickly and efficiently. Games...
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    About this property
    MEADOW'S EDGE COTTAGE - One of a row of 4 luxury cottages accessed through a cloistered passageway, a truly wonderful holiday experience awaits in Meadow's Edge, with its country style open plan kitchen, dining area and sitting room, the large feature fireplace with its working wood burning stove,...
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    Location Information
    Pickering, North Yorkshire YO18 8HY
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Exchange rate: 1 British Pounds = 1.22 U.S. Dollars
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