House vacation rentals in Helmsley

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Popular amenities for Helmsley house rentals

House rentals with a pool

Superhost
Home in The Bay Filey,
4.78 out of 5 average rating, 9 reviews

Silversands House at The Bay Filey - sea views

RichardRating, 5 stars10 months ago
Great place to stay with beautiful view and a great space outside for the kids to play
Superhost
Home in Primrose Valley
4.93 out of 5 average rating, 14 reviews

The Lookout @ The Bay Filey sea view, dog friendly

HazelRating, 5 stars1 month ago
We had a wonderful stay with our 6 month old baby. Ideal location for the beach, just a short walk down the hill. Also only a short walk to the amenities. Very dog friendly. The host was responsive and answered all our questions quickly. Had such a relaxing stay and especially loved the view from the master bedroom. We would love to return. Thank you!
Guest favorite
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 favorite
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, 78 reviews

three bedroomed house with stunning sea views

SueRating, 5 starstoday
Wonderful place to relax with friends. Really enjoyed the terrace and the views. Comfortable beds. A very attractive holiday park estate with a great feel. So close to the beaches and beach cafe. Richard very responsive and helpful. A perfect week.
Top guest favorite
Home in North Yorkshire
4.96 out of 5 average rating, 141 reviews

Lobster Pot -Award Winning Complex- The Bay, Filey

MattRating, 5 stars2 weeks ago
The place was lovely, a short walk to the lovely beach was the main draw. A good location to explore nearby towns by car. The additional of the on site swimming pool was great. The house the comfortable and great space for the 4 of us. Andree was very friendly and knew if we needed anything we could get in touch. Thanks.
Guest favorite
Home in Cayton Bay
4.9 out of 5 average rating, 135 reviews

Brand new 2021 ABI WINDERMERE STATIC Cedar 1

CarolineRating, 5 stars3 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.
Guest favorite
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.

Weekly house rentals

Guest favorite
Home in North Yorkshire
4.96 out of 5 average rating, 68 reviews

Old Coastguard Station with Stunning Sea Views

GillianRating, 5 stars1 week ago
Superb property with incredible views. Helen was an extremely friendly and responsive host. We cannot wait to return.
Top guest favorite
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!
Top guest favorite
Home in Kilburn
5 out of 5 average rating, 26 reviews

Dolittle Cottage, North Yorks

SouadRating, 5 stars5 days ago
We had such a lovely stay at the Dolittle Cottage. The house was clean, cozy, and exactly as described, but what really made it special were the thoughtful little touches. We were greeted with fresh flowers, and our kids were absolutely delighted to find toys waiting for them — such a kind and considerate gesture that made us feel truly welcome. Thank you for making our stay so comfortable and memorable.
Guest favorite
Home in Pickering
5 out of 5 average rating, 48 reviews

The Barn at Noelle's Cottages

SuzanneRating, 5 stars1 month ago
I wouldn’t hesitate to recommend a stay at The Barn. The property was immaculate, beautifully furnished and very well equipped. The garden as well as the house was spacious and both felt very private and tastefully appointed and allowed us a relaxing and comfortable stay. The location was perfect for exploring this part of North Yorkshire where there is so much to see and do.
Top guest favorite
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 favorite
Home in North Yorkshire
5 out of 5 average rating, 12 reviews

Little Fox Cottage

AllyRating, 5 stars2 months ago
We had a lovely short break. The cottage is located perfectly for visits to the coast and local towns and villages. The courtyard garden was secure for the dog and lovely to sit in the sunshine. The cottage had everything we needed and Adrian was really helpful. Thank you for having us.
Superhost
Home in North Yorkshire
4.82 out of 5 average rating, 44 reviews

Exceptional Goathland House, West View Mews

BethRating, 5 stars2 weeks ago
We had a lovely weekend away staying here! Great location within pickering, close to the restaurants, supermarket and lovely fish and chip shop just round the corner! The house was gorgeous, very clean and good kitchen. We especially enjoyed the hot tub, which was also very clean and private, and the additional outdoor dining space was very nice! Kirsty was a great host - very friendly and responded to questions promptly! Overall a great weekend stay and we would definitely come back!
Top guest favorite
Home in Felixkirk
5 out of 5 average rating, 16 reviews

Luxury country house

ChantelleRating, 5 stars1 week ago
We had a great visit to Yorkshire, the house and garden were beautiful. The village was easily accessible for what we wanted.

Private house rentals

Top guest favorite
Home in Bainbridge
4.95 out of 5 average rating, 43 reviews

1 bedroom bolt hole in the heart of the Dales

AlastairRating, 5 stars2 weeks ago
Spent a joyous week at Chantal's place in Bainbridge. It was cute, cosy, comfortable, quiet, stylish and well-appointed. Chantal was very attentive and had loads of great recommendations. Bainbridge is excellently situated for exploring the northern Dales and there are great walks to be had starting out from the village itself: the gentle climb up to tranquil Semer Water was a particular highlight.
Guest favorite
Home in City Centre
5 out of 5 average rating, 6 reviews

Minster View Townhouse

PepiRating, 5 stars4 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.
Top guest favorite
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 favorite
Home in Boathouse Yd
4.98 out of 5 average rating, 42 reviews

Old WatchHouse spacious seaviews

PaulRating, 5 stars1 week ago
The place is in a fantastic location with beautiful views across the harbour. The rooms are spacious, clean and homely. Great pub The Cod and Lobster has a great selection of beers and a huge Gin list. The food there is fantastic and reasonably priced. We will be going back next year and looking forward to staying at the Old Watch House again!!
Guest favorite
Home in Snape
5 out of 5 average rating, 6 reviews

Ramblers Barn, Snape, North Yorkshire

StevenRating, 5 stars1 month ago
Absolutely superb accommodation with a friendly, responsive, helpful host. The kitchen facilities are top quality. The accommodation is spacious, modern, and clean. The location is very quiet and peaceful. Central location with moderate drive to places we wanted to visit (e.g. Fountains Abbey). Will definitely choose Ramblers Barn again when visiting this area.
Guest favorite
Home in North Yorkshire
5 out of 5 average rating, 24 reviews

In the heart of Whitby!

GailRating, 5 stars2 weeks ago
Absolutely amazing views of Whitby from lounge and bedrooms. Beautifully decorated. Had everything you could possibly want and was spotlessly clean.Perfect!
Top guest favorite
Home in Dacre
5 out of 5 average rating, 63 reviews

Spinney Cottage, Pateley Bridge

MandyRating, 5 stars3 days ago
Perfect spot to relax and unwind. The Spinney is beautifully furnished and plenty of room for 4. Rosie and her family are lovely.
Top guest favorite
Home in North Yorkshire
4.98 out of 5 average rating, 53 reviews

Charming 2-bedroom cottage with river views

VanessaRating, 5 stars1 month ago
Lovely accommodation, great location. Would thoroughly recommend.

Quick stats about house rentals in Helmsley

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$16,719 GYD before taxes and fees

  • Total number of reviews

    470 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

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  2. United Kingdom
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  5. Helmsley
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