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Holiday Cottages in Helmsley

Find 207 available offers from 12 partners
Helmsley
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Helmsley
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Popular Filters to discover the perfect holiday home in Helmsley

House
2 Adults
Pets allowed
Hot tub
Pool
Cottage
Cabin

Helmsley letting cottages: For your slice of Yorkshire

Explore one of North Yorkshire's most attractive destinations with you very own Helmsley accommodation. Ancient ruins, sweeping vistas and friendly people make this a place you simply don't want to miss.

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Best holiday lettings with a pool

A swimming pool is a holiday home staple, and with 8% of the holiday rentals in Helmsley providing pool access, there are plenty of great options from which to choose. Get ready to take a dip and dive into the top offers for accommodation with private pools in Helmsley.

Cottage  Helmsley
21 Jun - 28 Jun
£143 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Pleasant Cottage in Edstone with Private Parking

Helmsley, Ryedale District, United Kingdom
Pool
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Cottage  Helmsley
2 Nov - 9 Nov
£235 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Wonderful Cottage in Sutton-Under-Whitestonecliffe with Sauna, Barbecue, Hot Tub

Helmsley, Ryedale District, United Kingdom
Free cancellation
Pool
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Cottage  Helmsley
1 Jun - 8 Jun
£162 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Brawby with Garden, Pool & Barbecue + Hill Views

5.0
Outstanding (5 ratings)
Helmsley, Ryedale District, United Kingdom
Pool
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Recommended pet-friendly holiday lettings

Bringing a canine companion along on your travels? Whether they're exploring the surroundings or finding a spot in which to snuggle up on the sofa, your pet will be welcome at one of the 57 dog-friendly holiday lettings in Helmsley.

Cottage  Helmsley
8 Nov - 15 Nov
-49%
£143
£73 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Wonderful Cottage in Helmsley with Barbecue & Garden

Helmsley, Ryedale District, United Kingdom
Pet-friendly
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Cottage  Helmsley
28 Sept - 5 Oct
-69%
£313
£98 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Helmsley with Barbecue & Garden

Helmsley, Ryedale District, United Kingdom
Pet-friendly
Details
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Cottage  Helmsley
11 Jan - 18 Jan
-39%
£198
£121 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Helmsley with Free Parking

4.0
Very good (1 rating)
Helmsley, Ryedale District, United Kingdom
Pet-friendly
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Best holiday homes with a patio or terrace

Want to admire Helmsley's vistas from the comfort of a holiday apartment, or enjoy private outside space while staying in a Helmsley holiday home? Take a look at our top lettings with balconies and patios in Helmsley and find the perfect accommodation for your stay.

Cottage  Helmsley
31 May - 7 Jun
£121 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Helmsley with Garden & Barbecue

Helmsley, Ryedale District, United Kingdom
Balcony/Patio
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Cottage  Helmsley
15 Jun - 22 Jun
£101 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Helmsley with Garden

Helmsley, Ryedale District, United Kingdom
Balcony/Patio
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Cottage  Helmsley
24 May - 31 May
£70 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Charming Cottage in Helmsley with Private Parking

Helmsley, Ryedale District, United Kingdom
Balcony/Patio
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Best holiday rental deals in Helmsley

Save up to 73%

Cottage Helmsley
25 Apr - 2 May
-15%
£113
£96 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Lovely Cottage in Helmsley with Garden

Helmsley, Ryedale District, United Kingdom
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Cottage Helmsley
23 Nov - 30 Nov
-72%
£301
£85 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Pleasant Cottage in Helmsley with Garden + Panoramic Views

4.0
Very good (1 rating)
Helmsley, Ryedale District, United Kingdom
Details
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Cottage Helmsley
16 Nov - 23 Nov
-73%
£253
£68 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Delightful Cottage in Helmsley with Rear Garden

Helmsley, Ryedale District, United Kingdom
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Find the perfect holiday letting from £37 per night by exploring the 207 properties on offer in Helmsley. Our search engine directly evaluates all the accommodation options to help you save up to 70%.

Recommended holiday lettings in Helmsley

Rent a holiday home, apartment or cottage in Helmsley from just £37 per night

Cottage Helmsley
24 May - 31 May
£143 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Cottage in Helmsley with Private Parking

5.0
Outstanding (10 ratings)
Helmsley, Ryedale District, United Kingdom
Details
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Cottage Helmsley
14 Jun - 21 Jun
£117 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Helmsley with South-Facing Garden

4.8
Outstanding (24 ratings)
Helmsley, Ryedale District, United Kingdom
Details
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Cottage Helmsley
7 Jun - 14 Jun
£124 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Helmsley with Private Parking

Helmsley, Ryedale District, United Kingdom
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House Helmsley
14 Oct - 21 Oct
-4%
£197
£189 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Helmsley with Terrace, Garden & Barbecue

5.0
Outstanding (59 ratings)
Helmsley, Ryedale District, United Kingdom
Details
Vrbo
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House Helmsley
24 Aug - 31 Aug
-4%
£175
£167 per night
House ∙ 6 guests ∙ 3 bedrooms

Spacious Holiday Home in Helmsley with Garden & Barbecue + Great Views

5.0
Outstanding (87 ratings)
Helmsley, Ryedale District, United Kingdom
Details
Vrbo
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Cottage Helmsley
21 Sept - 28 Sept
-38%
£168
£105 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Helmsley with Terrace, Garden & Barbecue

4.8
Outstanding (65 ratings)
Helmsley, Ryedale District, United Kingdom
Details
Vrbo
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Cottage Helmsley
25 Apr - 2 May
£90 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Beautiful Cottage in Helmsley with Second Patio

5.0
Outstanding (2 ratings)
Helmsley, Ryedale District, United Kingdom
Details
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Cottage Helmsley
6 Dec - 13 Dec
-77%
£507
£117 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Cottage in Helmsley with Garden + Castle View

Helmsley, Ryedale District, United Kingdom
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Cottage Helmsley
23 Nov - 30 Nov
-76%
£362
£89 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Helmsley with Garden & Terrace

5.0
Outstanding (1 rating)
Helmsley, Ryedale District, United Kingdom
Details
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Budget-friendly Holiday Homes in Helmsley

Find Fantastic yet Cheap Lettings

Cottage Helmsley
26 Apr - 3 May
-37%
£211
£134 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Beautiful Cottage in Helmsley with Free Parking

Helmsley, Ryedale District, United Kingdom
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House Helmsley
3 Nov - 10 Nov
-32%
£264
£179 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in Helmsley with Garden

Helmsley, Ryedale District, United Kingdom
Free cancellation
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Cottage Helmsley
11 Jan - 18 Jan
-51%
£664
£329 per night
Cottage ∙ 14 guests ∙ 5 bedrooms

Cottage in Helmsley with Large Patio

Helmsley, Ryedale District, United Kingdom
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Top-Rated Lettings and Properties in Helmsley

Book Holiday Letting Offers with the Highest User Rating

Bed and breakfast Helmsley
28 Nov - 5 Dec
£132 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom

Beautiful B&B in Helmsley with Garden

5.0
Outstanding (13 ratings)
Helmsley, Ryedale District, United Kingdom
Details
Expedia
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Bed and breakfast Helmsley
28 Nov - 5 Dec
£132 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B in Helmsley with Garden + Garden View

4.9
Outstanding (10 ratings)
Helmsley, Ryedale District, United Kingdom
Details
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Cottage Helmsley
19 Jul - 26 Jul
£320 per night
Cottage ∙ 8 guests ∙ 1 bedroom

Beautiful Cottage in Helmsley with Garden + Castle View

5.0
Outstanding (1 rating)
Helmsley, Ryedale District, United Kingdom
Details
Expedia
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Popular holiday rental amenities in Helmsley

  • Pet-friendly (57)
  • WiFi (183)
  • Parking (35)
  • Fireplace (66)
  • Garden (154)
  • Pool (14)
  • Dishwasher (85)
  • Kitchen (115)
  • Microwave (88)
  • Balcony/patio (51)
  • Hot tub (15)
  • TV (174)

In Helmsley, there are plenty of choices in case you want to book a rental that welcomes pets. Cottage are the most pet-friendly type of accommodation in Helmsley. A night in a pet-friendly property there is, on average, £232. More than a quarter of the pet-friendly holiday lettings are located less than 2 kilometres away from the city centre.

The Weather in Helmsley

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13 days 13
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16 days 16
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14 days 14
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12 days 12
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14 days 14
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15 days 15
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14 days 14
Jan.
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May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above is a weather diagram for Helmsley. July is the hottest month in Helmsley, with average daily maximum temperatures of 18°. Conversely, February is the coldest month in Helmsley, with temperatures falling below 1°. April is the driest month in Helmsley.

7-Day Weather Forecast in Helmsley

Mon, 20 May
15°
14°

0%

5 h

15 km/h

Tue, 21 May
16°
15°

90%

0 h

7 km/h

Wed, 22 May
16°
13°

90%

0 h

22 km/h

Thu, 23 May
12°
12°

90%

0 h

39 km/h

Fri, 24 May
17°
13°

20%

1 h

20 km/h

Sat, 25 May
17°
15°

10%

0 h

20 km/h

Sun, 26 May
14°
13°

20%

0 h

18 km/h

Accommodation options for your holiday in Helmsley

In Helmsley, more than two-thirds of the 207 holiday accommodation options in Helmsley are cottage, which represent 75% of the listed properties. Cottage here have an average price of £213 a night as well as a median size of 129 m². Furthermore, the majority of cottage in Helmsley can accommodate 6 people, which makes Helmsley an ideal holiday spot for medium-sized groups and families. Travellers interested in another type of accommodation can, with HomeToGo's fantastic range, also find an ideal house rentals for them. This property type is the second most popular accommodation option in Helmsley. These properties cost £251 per night, on average, and have an average size of 84 m².
Where to find the best food in Helmsley?

Food and drink in Helmsley

From cosy cafes to fine dining, you'll be spoiled for choice when you visit Helmsley. The Yorkshire countryside is known for its farming prowess and many of the restaurants rely heavily on local produce. Start your day with a fresh pastry from Auntie Anne's Castlegate Bakery. The family-run business is a stalwart of the town and sells everything from pies to puddings.

Crema Coffee House or Porters Coffee Shop are the perfect places to stop for a spot of lunch after taking in the attractions and scenery of the town. Once evening draws in, why not tuck into some fish and chips at the award-winning Scotts of Helmsley? As if that wasn't enough, the town is home to the Traditional Sweet Shop as well as butchers, several shops and a brewing company where you can go to sample a little of the local tipple.

What are the best places to discover the arts and culture of Helmsley?

Arts, culture and attractions in Helmsley

Despite its small size, there is much to explore and experience in this town which dates back hundreds of years. The imposing castle ruins are simply a must. You can learn about its fascinating history, including the role which the castle played in the English Civil War. The Helmsley Arts Centre is a bustling local enterprise with a cinema and theatre. They also host exhibitions, talks and classes suitable for people of all ages. The walled garden, constructed in 1759, is now aiming to conserve endangered plants. Even if you aren't a budding horticulturalist you can appreciate the garden's natural and curated beauty.

If you have an interest in animals and preservation then take a trip to the National Centre for Birds of Pray to see the largest collection of birds in the North of England. You can also take a dip in the town's outdoor swimming pool if you're visiting Helmsley in the summer months.

Where are the unique attractions in Helmsley?

Exploring the wider area

North Yorkshire is one of the most picturesque counties in the UK. Famed for its historic towns and national parks, there's lots to see within an hour from Helmsley. York is a beautiful northern city famous for its Minster. Along with the castle and Ruins of St Mary's Abbey, York has plenty to keep you busy for a full or half-day trip.

Skipton and Harrogate are other fantastic destinations in their own right. The North York Moors and Yorkshire Dales are both close to the town of Helsmsley and are popular with walkers, cyclists and those looking to just enjoy these green and pleasant lands.

Information about holiday rentals in Helmsley

🏡 Holiday homes available 207 rentals
💳 Discounts available up to 70%
🌙 Nightly prices from £37
⭐ Popular amenities Pets allowed, Internet and Parking
🐾 Pet friendly rentals 57 properties
🏊 Holiday rentals with pools 17 properties
2 reviews
Helmsley holiday rentals have an average rating of 4/5 across 2 reviews left by travellers.

Frequently Asked Questions

How many holiday homes are available to rent in Helmsley?

Currently there are 207 holiday rentals in Helmsley to browse and book for your next trip.

What is the most popular holiday home amenity in Helmsley?

The most popular amenities among our customers in Helmsley are Pets allowed, Internet and Parking.

How many holiday homes with a pool there are on offer in Helmsley?

Holiday homes with pools are 8 of all offers in Helmsley for an average price of £300 per night.

Am I allowed to bring my pet during my stay in a Helmsley holiday home?

Dogs are welcome in Helmsley with 57 pet-friendly holiday homes.

What is the best time of year to travel to Helmsley?

Sun lovers should visit Helmsley in July and August to enjoy the warmest weather.

How do I find deals on holiday homes in Helmsley?

You can find brilliant bargains on holiday lettings in Helmsley with the nightly price of a rental starting at just £37 - and HomeToGo has launched plenty of features that mean it's a piece of cake to locate the best deals. When choosing the dates for your break, try a search using HomeToGo's flexible dates technology to quickly locate low-price date options and see savings of up to 70%. In addition, HomeToGo's 'distance from' filter lets you locate hidden treasure holiday rentals in great value, lesser-known spots that are just as close to the area of your choice, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Start your search as soon as possible to make the most of a wide range of offers and the best deals - and do so free from stress by selecting HomeToGo's 'free cancellation' filter when you search.

What are the pros of booking a holiday letting in Helmsley with HomeToGo?

From serenity away from the crowds to more space for relaxing with your family, friends or partner, holiday homes in Helmsley bring plenty of bonuses. HomeToGo shows you genuine ratings from verified visitors, and searching is safe, simple, and hassle-free - so with 207 deals from 12 providers in the area, you're sure to find the right type of accommodation with the amenities and features you need in Helmsley.

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