Plan a trip to Helmsley, and get ready to fall in love with its vibrant character. It is a quintessential market town in North Yorkshire county characterized by well-preserved castle ruins, cozy tea rooms, and beautiful walled gardens. It is also steeped in history, and you can learn more about it when you visit places like Helmsley Castle. If you’re looking for a relatively relaxing afternoon activity, take a stroll through the flower fields and apple orchards at Helmsley Walled Garden. With plenty of things to do in this English market town, you’ll need a place to stay for a few days. Read on to learn more about the best Airbnb vacation rentals in Helmsley, UK.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Cherry Tree House (from USD 1141)
This residential home perfectly captures the market town’s vibrant character, featuring an exterior of red bricks and well-groomed evergreen shrubs. Vintage touches, such as the intricately carved cabinets, cherry wood dining room set, and a full-length arched wall mirror, fill the abode’s entire interior. Plus, it features a contemporary kitchen where you can rustle up a meal any day.
A family of eight is sure to have a good night’s sleep in the four distinctive bedrooms. You can also browse the internet or watch TV if you plan on staying indoors. For other forms of relaxation, head to the garden and savor an afternoon tea on the patio.
Top guest reviews
Amenities & Room:
beds comfy lots of indoor seating good wifi kitchen had everything you could needa good kitchen comfortable sitting room good library and local information and good bedsthe house is comfortable and as describedHost:
the owner was "quackers" in a fabulous wayRead more reviewsLocation:
a fabulous social house just a couple of minutes walk from helmsley centre
2. Converted carriage with a backyard (from USD 150)
If you’re looking for a unique vacation experience, consider booking a few days’ stay at this rental for four. It was a Victorian railway carriage built in the 1800s but was later converted into a self-catering property. The space inside is spacious enough to fit two bedrooms, a full kitchen, a sitting area, and a bathroom. It also offers reading materials and WiFi to keep everyone entertained.
You can also walk to the beautiful garden for some fresh air. Guests can avail themselves of free parking on the premises.
Top guest reviews
Amenities & Room:
the beds were very comfortable and the hamper was a nice touchbeautiful little railway carriage with a pull down double bed plus two bunkslouises garden is very pretty & her breakfast was incredible we stuffed our facesCleanliness:
spotlessly clean and very unique stayit was beautifully clean in arrival and we received a lovely welcomemeticulously clean great location and amenitiesthe carriage is spotlessly clean and has everything you needfantastic stay spotlessly clean and great locationHost:
most helpful and charming hosts who made us feel at homeour hosts made us feel very welcomelouise is a very thoughtful and considerate hostabsolute gem of a find and the hosts are so friendly and communicativelouise and richard are lovely hostsRead more reviewsLocation:
excellent location and great experience in a unique environmentfacilities and location were excellentgreat location in the centre of helmsley and ideal for exploring north yorkshirebeautifully restored and equipped and great location in the heart of helmsleyfantastic location if you are staying in helmsley or going to the north moors national park
3. Newly renovated cottage with a walled garden (from USD 170)
Enjoy days of sun and gentle breezes at this stone cottage adequate for a small group of four. It has a lovely walled garden and courtyard where you can spend lazy afternoons or quiet mornings. It has been refurbished recently by the hosts to give guests a five-star holiday experience.
You can whip up hearty meals in the fully equipped kitchen provided with a refrigerator, microwave, and cooking basics, or lounge in the spacious sitting room fitted with new pieces of upholstered furniture and rugs. Of course, you are also welcome to celebrate with a few drinks in the sunroom.
Top guest reviews
Cleanliness:
great property very clean and tidy really impressedthe house: super clean bright & comfortablevery clean and the host provided clear information on the cottage and check-in was very easyoverall thought the cottage was very homely and relaxing clean too we would returnRead more reviewsLocation:
great location very comfy bedcottage was excellent in a good location right in the heart of helmsley
4. h-century rental in the heart of Helmsley (from USD 106)
This lovely rental is tucked away on the first floor of a 17th-century longhouse and features one bedroom for two guests. It is located in the heart of Helmsley, giving you the luxury to unravel Yorkshire’s unique offerings. Besides the cozy bedroom, it also features a tiny kitchen equipped with everything you might need to cook your daily meals.
You can also relax in the sitting room fitted with double-hung windows that bring in light and offer magnificent views of Helmsley Castle. Other amenities, such as WiFi, TV, and a dedicated workspace, only make the stay all the more convenient.
Top guest reviews
Amenities & Room:
beautiful apartment with all amenitiesbeautifull sitting room with great viewssitting room is particularly nice and cosy with a fabulous view of the castlefantastic spacious and clean apartment situated centrally with a beautiful view of the castlewe absolutely loved this apartment from the location to the amenities personal touches and homeliness it’s gorgeousCleanliness:
it was clean comfortable and very welcomingit was clean with extra touches to make your stay even betterit was spotlessly clean when we arrived and is very comfortable and warmvery clean and fantastic viewimmaculately clean beautiful bedding and thoughtful touchesHost:
the hosts were great too accommodating me at the last minute and responding very quickly to all messagessimon was very helpful and responsivesimon was hospitable and helpfulthe host was very thoughtful and left tea coffee biscuits and fruit which came in really handyRead more reviewsLocation:
perfect location in the heart of helmsleya beautiful flat a great locationgreat apartment in an excellent locationsimon's place was in a wonderful locationit was the perfect location for us visiting family in helmsley
5. Handsome cottage with beautiful views (from USD 175)
Escape with your friends or family to Yorkshire, and soak up Helmsley’s wonderfully relaxed vibes. For a place to stay, opt for this newly renovated cottage that can sleep up to six guests. The interior is bright and spacious, thanks to the glass doors, windows, and sloped ceilings. If you’re making food for everyone, the kitchen is lined with cabinets and fitted with appliances and other cooking basics.
There’s also a cozy sitting room adorned with colorful rugs and rattan furniture, which leads to the garden and conservatory. You can also access the WiFi and TV if you decide to take a break from exploring the outdoors.
Top guest reviews
Amenities & Room:
beds were very comfortable with lovely crisp linenthe cottage itself is beautiful with everything you need for a comfortable staythe lounge/conservatory space was amazing and the beds were comfyplenty of space for 6 people having 2 different living rooms with tvs was a great little touchso comfortable we just stayed in one of the nights and enjoyed our surroundingsCleanliness:
beautifully cleaned prior to our arrivalthe house was very clean to covid regulations and had plenty of cleaning materials/soap/hand sanitizerbeautifully furnished and decorated with comfy beds and lots of clean towelswarm cosy spotlessly cleanthe house was impeccably clean which is so important in these times and we felt safe thereHost:
the hosts are superb on every levelolivia the host was really quick to respond to any questions and was very helpfulolivia was a really great host with great communicationolivia and ness were very quick to respond to enquiries and were so helpfulolivia is a fantastic host very thoughtful and brilliant at communicating with usRead more reviewsLocation:
the location is amazinggreat place in a great locationfantastic house in a beautiful locationthe location is perfect literally a 2 minute walk to pubs shops restaurants and cafesa beautiful spacious house in a perfect location right in the heart of helmsley
6. Charming home with fireplace (from USD 139)
This house has been around since the 1700s, and you can quickly discern this fact from its stone-clad facade and raw interior. It features one bedroom and one bath, perfect for a couple on a romantic getaway. You’ll never be bored during your stay as this beautiful abode also comes with reliable WiFi and TV. You can even spend chilly nights reading or snuggling in front of the cozy fireplace.
Looking to surprise your loved one with a romantic dinner? You may whip up tasty meals in the kitchen equipped with a refrigerator, microwave, and other cooking basics.
Top guest reviews
Amenities & Room:
we had a lovely stay at alex's wonderful cottage it is very comfortable and homelyCleanliness:
it has historic charm yet is comfortable clean and well equippedcottage is quaint clean bedrooms and bathroombed was comfy and clean as was rest of the housethe cottage was spotlessly clean and alex was a great hostthe cottage was clean comfortable and cosy and located perfectly for exploring the townHost:
alex was a very gracious hostshe was extremely helpful in welcoming us and in answering our questions along the wayalex was very welcoming and helpfulalex was a great host and very easy to contactalex the host had thought of everything needed for a comfortable stayRead more reviewsLocation:
great location in the villageexcellent base and location for exploring helmsleyexcellent location for walking and shopslovely place in a great locationthe centre of the village is within a 2 minute walk with many nice restaurants and pubs
7. Pet-friendly house with a lovely balcony (from USD 179)
This newly renovated three-bedroom rental welcomes a maximum of six guests and two medium-sized dogs, allowing you to enjoy your Helmsley holiday with your fur babies. It is in a coveted area that gives you quick access to eclectic shops and trendy restaurants. In terms of comfort and convenience, this rental features a contemporary kitchen where you can prepare tasty meals for your companion.
Besides that, it boasts a lovely dining area that connects to the sunlit living area with two comfy sofas and double-hung windows. If you’re looking for a place where you can take in the fresh air, head to the balcony or relax on the patio.
Top guest reviews
Amenities & Room:
comfortable cottage with lots of space stocked kitchen and good en suite bathrooms and parking for one carhaving two comfortable areas to sit and relax was a bonus with a diverse group thanks amandathree good sized bedrooms all en-suite comfortable lounge sunroom separate dining room and a well-equipped kitchenthe decor is modern and stylish whilst being homely and very comfortableCleanliness:
everything very clean and comfortablea very clean and beautiful cottageit was spotlessly clean and had everything we could possibly needwarm welcoming and cleanamanda's property was wonderfully clean comfortable and equippedHost:
amanda is a great host…amanda is an excellent host super quick responses and friendlyamanda our host kept in touch to make sure we had everything we neededsuper host with excellent communicationamanda is very helpful and responds at very short notice and is very accommodating at short noticeRead more reviewsLocation:
great location 2 minutes from helmsley market squarea fantastic family option in a wonderful locationthe location is excellent and we hope to come backperfect location within helmsley just a 5 minute walk to all this lovely town has to offeryou can easily walk to helmsley and there are so many lovely villages to drive to nearby
8. Spacious apartment with a private backyard (from USD 246)
What better way to explore Helmsley than with your family or friends? This rental has enough space for all of them, accommodating up to eight guests, and they can choose to sleep in any of the four bedrooms. The kitchen is simple but fitted with modern appliances and cooking basics. If you need to catch up on some work, feel free to access the WiFi and use the dedicated workspace.
The little one’s comfort is also ensured, with amenities such as a cot, baby safety gates, and a high chair. Fur babies are allowed on the property, and they can even play or run around the private backyard, though bear in mind that it’s not fully fenced.
Top guest reviews
Amenities & Room:
this is a great house - plenty of space and a great kitchenCleanliness:
great house spotlessly clean and loads of spaceit is very clean and spaciouseverything was very clean and the communication from the owners was spot oncomfy clean and warm and good locationgreat place very clean well equipped and bigger than the photos suggestHost:
great place great home and great hosts 5 starbeautiful spacious house and helpful friendly hostshosts were great too especially with communicationthe hosts were very flexible with regards to check in and out which was very helpfulnice spacious house with accomadting hostsRead more reviewsLocation:
great central location we would returnperfect location just a short 2 minute walk into the centre of helmsleybig house in a great location to explore yorkshiregreat location and good value for moneylovely spacious house in a great location perfect for a family break
9. Tastefully designed property for four guests (from USD 108)
No need to commute or drive to see what makes this town unique, as this pleasant residential home is close to everything Helmsley has to offer, such as restaurants, bars, and tea rooms. It features two charming bedrooms and one bath, perfect for a small family or a group of four friends.
Let out your inner chef by cooking delicious meals in the fully equipped kitchen. There’s also a dedicated parking space on the premises if you plan to take a vehicle with you.
Top guest reviews
Amenities & Room:
you can expect warm welcome and a comfortable stay in this cosy cottageso cosy and comfortable and would recommend staying in this cottagevery warm and cosy with all you need for a comfortable staywarm comfortable and so convenientCleanliness:
good clean cottge in the centre of helmsleylovely clean cottage with very central locationnice and clean cottage a great valuethe cottage itself is clean and homely with some lovely little welcoming touches and jacqui is very helpfulspotlessly clean and well equipped cosy central heating and super comfortable bedsHost:
jacqui is a great hostjacqui is a great hostexcellent communications with host jacquigreat host easy to communicate withjacqui was super quick to reply and provided really clear and helpful info for checking inRead more reviewsLocation:
amazing location in a great villagesuper location couldn't be closer to the market square and beautifully decoratedfantastic place in a perfect locationwalking distance to castle and bird of prey centre and close to other north moor attractionsit’s in an ideal location for visiting helmsley and the surrounding area
10. Lovely apartment with a sunny garden area
If you’re intent on exploring the best of this quaint market town, consider booking a weekend stay at Bondgate Apartment. It has an interior that exudes a country vibe, with cozy bedrooms that guarantee hours of undisturbed sleep.
Cooking will be fun and easy knowing that the kitchen is already equipped with everything you might need, including a stovetop, oven, and toaster. You’ll also love the rental’s beautiful garden where you can sip a glass of red wine or enjoy a cup of tea.
Helmsley, England, United Kingdom
16.84 km (10.5 mi) from Flamingo Land ResortSuperhost
Accommodates: 3
Top guest reviews
Amenities & Room:
lovely outdoor space and open air pool a short walk awayCleanliness:
very comfortable apartment and spotlessly cleanthe apartment is very clean and well presentedwe enjoyed a friendly welcome and the accommodation was clean and well equippedcomfortable spacious flat convenient for local facilitiesHost:
very attentive hosts we would highly recommendmark and gail were very friendly hosts and had great communication throughoutRead more reviewsLocation:
this is the perfect locationgreat location spacious flat free ample parking outside the doorit's in a great location for days out and with cafes shops pubs and restaurants on the doorstep
Make the most of your Helmsley holiday
Although known for its bustling market square, Helmsley also makes a spectacular destination for history lovers and tea connoisseurs. Make the most of your holiday time, and book an accommodation from our list.
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