House holiday rentals in Pickering

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Popular amenities for house rentals in Pickering

House rentals with a pool

Guest favourite
Home in Ebberston
4.8 out of 5 average rating, 15 reviews

Family sized cottage, sleeps 4 and swimming pool

LucyRating, 5 stars2 months ago
Absolutely loved our stay at Cliff House with Jacquline. Beautiful location, swimming pool was such a bonus for the children, they loved it! The grounds were fantastic, such a lot to explore, our children loved the chickens and climbing frame and the private wood was great for hide and seek. Jacquline was such a great, friendly host and gave us great advice about visiting York. She even arranged an Easter egg hunt for our children. We had a wonderful time and would definitely recommend.
Guest favourite
Home in North Yorkshire
4.92 out of 5 average rating, 143 reviews

Salty Kisses, The Bay, Filey

KarenRating, 5 stars3 weeks ago
Had a lovely Bank Holiday weekend at Salty Kisses with my family. The house was clean, well equipped and in a great location. Joanne was a very good host and emailed all the information I needed. Would definitely recommend.
Superhost
Home in North Yorkshire
4.88 out of 5 average rating, 77 reviews

three bedroomed house with stunning sea views

GemmaRating, 5 stars3 months ago
Fantastic stay at Seaspray. Richard sent very helpful instructions before we arrived, not only detailing the check in and how to find the property, but everything we could have needed to make us feel at home. The home was beautiful and we were always warm. The weather turned up for us so we were able to make use of the great location for walls and the sea. You are very close to Filey and with Scarborough and Bridlington only slightly further, so we fit in all 3. We will be coming back. Wonderful state would definitely recommend
Top guest favourite
Home in North Yorkshire
4.96 out of 5 average rating, 140 reviews

Lobster Pot -Award Winning Complex- The Bay, Filey

NicolaRating, 5 stars2 weeks ago
Andrée was so warm, friendly and accommodating. The house is absolutely stunning, spacious, clean, well maintained and is SO well equipped. The house had absolutely everything a family might need at the beach, including chairs, beach toys, an array of outdoor games, parasols, beach mats…the list goes on! An amazing selection of board games in the house too. The location is incredible too. My children adored the house and we can’t wait to come back again soon.
Guest favourite
Home in Cayton Bay
4.9 out of 5 average rating, 135 reviews

Brand new 2021 ABI WINDERMERE STATIC Cedar 1

CarolineRating, 5 stars2 weeks ago
Great location! perfect for beach, dog walks and bus to Scarborough /Filey etc. if not driving. Caravan had everything we needed including dishwasher/air fryer/microwave and plenty of dishes/cups/glasses/ cutlery etc. Kim was a very responsive host. Situated near shop playground and pool it’s in ideal spot on the site. Car can be parked right across from caravan so easy to walk on grass to/from caravan.
Top guest favourite
Home in Birdforth
5 out of 5 average rating, 13 reviews

Mill House - Birdforth Hall Holiday Cottages

BradRating, 5 stars1 month ago
Myself, 9 others and 1 small dog booked on of Sue's fantastic cottages for a reunion weekend. Sue was very easy to communicate with, gave us the guidebook ahead of time virtually for any queries (we were very interested in the pizza oven and games room) Facilties were excellent, we were lucky that no other cottages on the site (only 3 others) were in use during our stay, so had free roam of the site and facilties. The local recommendations were brilliant. We went to the old black bull down the road for dinner on the first night and then again for roast dinner on Sunday - mega The house itself is just as shown in the photos, more than comfortable to sleep and house 10 of us for the weekend. Special mention to the hottub, (which is private for your house and I believe comes with all houses) and to Paul who was more than helpful coming to our rescue and reviving out pizza night when we experienced some issues with the oven. 10/10 would go again.
Guest favourite
Home in North Yorkshire
4.88 out of 5 average rating, 66 reviews

Cosy 2 bedroom river/coastal retreat in whitby

MartreceRating, 5 stars1 week ago
Everything was perfect! The cottage is cosy and had all the amenities needed. It was clean and just a 30min walk in to Whitby. We loved our stay and would definitely recommend.
Superhost
Home in Pickering
4.92 out of 5 average rating, 12 reviews

The Grange | sleeps 12 - Swim Spa -Dog Friendly 5*

LauraRating, 5 stars12 months ago
Expensive but worth every penny for our 4 generation trip. Rooms for exuberant kids and quiet rooms for 90+ years old great grand parents. Large sociable kitchen diner . Swim spa at 35c so great for the Californian kids.

Weekly house rentals

Top guest favourite
Home in North Yorkshire
4.96 out of 5 average rating, 45 reviews

Old Town Luxury, By The Sea - 3 en suite bedrooms.

MjRating, 5 starstoday
This is a haven of tranquility. Walk through the doors and you feel at home. So beautifully decorated, absolutely perfect in every way. We are keen cooks, love to spend time in the kitchen making meals and enjoying company of friends. The kitchen was perfectly equipped with all you need. Peter is an outstanding host and offers support instantly. We had a slight glitch with the internet (not Peter’s fault!) and he was so helpful and supportive. We love the place. Seriously LOVE! We will be back and look forward to being back!
Top guest favourite
Home in Thornton-le-Clay
5 out of 5 average rating, 27 reviews

Luxurious Cottage in North Yorkshire

MikeRating, 5 stars3 weeks ago
Fantastic out-building conversion, with a private garden and fenced area separating the property from neighbouring houses and the shared drive. The property is modern, extremely spacious and very well appointed, with pretty much everything you could think of.....Flo even left us some wood for the fire pit in the garden and fuel for the Eco-Boiler, as well as Kitchen essentials. Comfy beds, spacious bedrooms (including an en-suite), and a stunning open plan living area that blew us away. There was very little in the village, but the quiet and peace suited us perfectly, and the area is beautiful. The recommendations for local places to visit were also greatly appreciated. Definitely somewhere we would recommend and return to if we are ever in the area again. Thank you for such a great visit.
Top guest favourite
Home in Hackness
5 out of 5 average rating, 41 reviews

The Stable Cottage

MelanieRating, 5 stars2 weeks ago
We had a peaceful few days at Liz and Nick’s cottage. It was spotlessly clean and extremely peaceful, being set in the most beautiful surroundings. The welcome hamper was a lovely touch and the home-baked cookies were delicious! Liz’s communication was excellent and she was very accommodating when we needed to change the days of our stay slightly. We would definitely recommend it to others.
Top guest favourite
Home in Rosedale Abbey
5 out of 5 average rating, 20 reviews

Pigin Cottage - Small, cosy, perfectly restored

DavinaRating, 5 stars6 days ago
Amazing location, easy walk up onto the moors or into Rosedale along the river valley. Beautifully restored and fitted out. Everything tool you could possibly need was provided in the kitchen. Peaceful seating area out the back and we loved seeing the rabbits and hearing the owls.
Top guest favourite
Home in Sewerby
5 out of 5 average rating, 54 reviews

Trinket - The Cliff Top Cottage

HelenRating, 5 stars4 days ago
This is a beautifully renovated cottage in a charming village away from the hustle and bustle of Bridlington. A very short walk to the cliff top walkway which has great views along the coast. The cottage was spotless and the lovely big bath was a highlight. Much appreciated the milk, buscuits and condiments provided for cooking too. There is a garage which I did manage to squeeze my car into but otherwise there is parking nearby. Would happily stay again if in the area.
Top guest favourite
Home in Rosedale Abbey
5 out of 5 average rating, 11 reviews

The Knoll

RebeccaRating, 5 stars1 month ago
Lovely place, very spacious with everything you need. The surroundings are peaceful and beautiful and there are a couple of pubs in walking distance.
Guest favourite
Home in North Yorkshire
4.9 out of 5 average rating, 20 reviews

Family Farm Country Paradise- hot tub break

BlakeRating, 5 stars2 weeks ago
what a little jem, nice a secluded with beautiful views. nice hottub. the interior was amazing and beautifully presented. will definitely be back.
Top guest favourite
Home in North Yorkshire
5 out of 5 average rating, 15 reviews

The Swiss Cottage, Pickering

RoseRating, 5 stars2 months ago
What a find! So central but private and very homely. We had a fantastic week either exploring the area or relaxing at home in front of the fire. Loved the house and the position which was so handy for the shops and restaurants … we will definitely be back. Carole is so kind and helpful :)

Private house rentals

Guest favourite
Home in North Yorkshire
4.96 out of 5 average rating, 67 reviews

Old Coastguard Station with Stunning Sea Views

MelissaRating, 5 stars2 weeks ago
Easy and stress free booking and check in. Lovely house with stunning sea views from the main living room. Would not recommend for anyone with mobility issues due to steep winding stairs, particularly to the 2nd floor where two of the bedrooms located. Also lots of steps to access beach/promenade. Otherwise we had a lively break away and would definitely book again when visiting Filey
Guest favourite
Home in City Centre
5 out of 5 average rating, 5 reviews

Minster View Townhouse

PepiRating, 5 stars2 days ago
This was an amazing house in the heart of medieval York. Not only that, but the house itself is 700+ years old and you can feel it's character through the amazing renovation that has been done! The Minster is visible from the windows of the property, so you know that the views are just breathtaking. There are plenty of amazing shops, cafes, restaurants, and other businesses in walking distance, while the world-famous Shambles street and market is 5 minutes away. Can't recommend this more.
Guest favourite
Home in Wilton
4.93 out of 5 average rating, 15 reviews

Prospect Farm Cottages - Sinnington Cottage

SarahRating, 5 stars1 week ago
Lovely cottage in a peaceful village setting. Exactly as the photos and while small, enough space for 2 people for a few days. Martin was very friendly and quickly responded and rectified the small issues I had.
Top guest favourite
Home in Whitwell-on-the-Hill
4.96 out of 5 average rating, 51 reviews

Snowdrop Cottage

BryonyRating, 5 stars1 week ago
Lovely cottage in a beautiful village and so easy to get in to York and other places. Loved the cafe in the village as well, super handy. All rooms beautifully decorated and everything we needed!
Guest favourite
Home in Newton-on-Rawcliffe
4.93 out of 5 average rating, 81 reviews

Idyllic Farm based cottage with hot tub

DonnaRating, 5 starstoday
We had the most wonderful stay at Wagtail Cottage. Beautiful surroundings and so peaceful. The cottage was spotless and we were left a thoughtful welcome hamper including much appreciated milk (in the fridge) for a cuppa after a long drive along with other lovely treats including some for our dog. The house manual was great giving lots of recommendations from places to visit to takeaways. We crammed a lot into our few days visiting the beautiful city of York, walking a very pretty trail from Rievaulx Abbey to Helmsley and back, Pickering and Whitby. All worthy of a visit. Communication with our host was excellent every time. Have nothing negative to say. Would definitely recommend and hope to come back in the future. Our little dog had the best time too.
Top guest favourite
Home in Dacre
5 out of 5 average rating, 63 reviews

Spinney Cottage, Pateley Bridge

MandyRating, 5 stars1 day ago
Perfect spot to relax and unwind. The Spinney is beautifully furnished and plenty of room for 4. Rosie and her family are lovely.
Guest favourite
Home in Robin Hood's Bay
4.93 out of 5 average rating, 72 reviews

Warm comfortable cottage,sea view from rear garden

GordonRating, 5 stars5 days ago
This is a lovely historic cottage at the very bottom of the hill in Robin Hood’s Bay, so literally a stone’s throw from the slipway to the beach. Perfect location to explore this special little place. The cosy living room is well set out then the first floor has the main bedroom (with an antique bed) and a door out to the back area with the picnic table. Lovely to take in the views of the bay in the evening and morning. Top floor has a good shower room and a twin bedroom. Within two minutes of the front door are several nice cafes, shops, a good restaurant, a bookshop and the beach. Hard to beat for location. Walking up the hill is hard work, but you only need to do that if you’re heading off. We had a problem sorting out the right key for the back door and Gordon and the housekeeper sorted it out immediately. It passed my wife’s cleanliness test - a lot of places she cleans herself when we arrive, but no need here. It was spotless.
Top guest favourite
Home in North Yorkshire
4.94 out of 5 average rating, 18 reviews

Stables Cottage

RichardRating, 5 stars2 weeks ago
Just had 6 nights at Murk Farm in the Stables Cottage with friends. Everything was fantastic. Accomodation was spotless and well furnished with everything you would need for a perfect stay. Overlooking undulating farmland, private and peaceful . Couldn't have asked for anything better. Joanna was the perfect host. Lovely cake left on our arrival. Definitely would return and recommend. Richard

Quick stats about house rentals in Pickering

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹3,471 before taxes and fees

  • Total number of reviews

    480 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  5. Pickering
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