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Helmsley Vacation Rentals

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In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Helmsley vacation rentals

Cottage | Interior
Ivy Cottage

Ivy Cottage

Ivy Cottage
3.5 star property
York
$465 nightly
The price is $558
Jan 19 - Jan 20
Total with taxes and fees
Ivy Cottage
Smart TV, offices
Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
2.0 star property
Helmsley
$766 nightly
The price is $766
Jan 11 - Jan 12
Total with taxes and fees
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Cliff House

Cliff House

Cliff House
3.5 star property
York
$576 nightly
The price is $691
Jan 13 - Jan 14
Total with taxes and fees
Cliff House
Cottage | Interior
29 Bondgate

29 Bondgate

29 Bondgate
3.5 star property
York
$562 nightly
The price is $674
Jan 13 - Jan 14
Total with taxes and fees
29 Bondgate
Room, Shared Bathroom (Dog Pod) | Exterior
The Little Hide - Adult Only Camping Pods

The Little Hide - Adult Only Camping Pods

The Little Hide - Adult Only Camping Pods
2.0 star property
York
9.2 out of 10, Wonderful, (148 reviews)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
United Kingdom
Michael
$62 nightly
The price is $74
Jan 11 - Jan 12
Total with taxes and fees
The Little Hide - Adult Only Camping Pods
Bar (on property)
Station Suites

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (23 reviews)
"The staff was very friendly and responsive. Location is great - right across from the Middlesbrough train station."
United States
Brett
$90 nightly
The price is $108
Jan 11 - Jan 12
Total with taxes and fees
Station Suites
Exterior
Cosy, 2 Bedroom Cottage in Guisborough Town Centre

Cosy, 2 Bedroom Cottage in Guisborough Town Centre

Cosy, 2 Bedroom Cottage in Guisborough Town Centre
North Yorkshire
10.0 out of 10, Exceptional, (2 reviews)
"It’s well situated and a nice place to stay. "
United States
jane
$118 nightly
The price is $118
Jan 11 - Jan 12
Total with taxes and fees
Cosy, 2 Bedroom Cottage in Guisborough Town Centre
Studio | Property grounds
Luxury Studio Cottage at Foot of Yorkshire Wolds

Luxury Studio Cottage at Foot of Yorkshire Wolds

Luxury Studio Cottage at Foot of Yorkshire Wolds
3.0 star property
York
10.0 out of 10, Exceptional, (2 reviews)
"This is a lovely place to stay.."
United Kingdom
Darren
$276 nightly
The price is $331
Jan 16 - Jan 17
Total with taxes and fees
Luxury Studio Cottage at Foot of Yorkshire Wolds
Interior
Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.

Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.

Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.
2.0 star property
Holgate
10.0 out of 10, Exceptional, (1 review)
"Absolutely brulliant property.. a home away from home"
United Kingdom
John
$196 nightly
The price is $223
Jan 10 - Jan 11
Total with taxes and fees
Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.
Premium bedding, individually decorated, individually furnished
Morndyke Shepherds' Huts

Morndyke Shepherds' Huts

Morndyke Shepherds' Huts
3.5 star property
Thirsk
9.8 out of 10, Exceptional, (19 reviews)
"Amazing place, thanks so much ! "
United Kingdom
Tom
Morndyke Shepherds' Huts
View from property
Goodramgate Apartments

Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (286 reviews)
"Very cute and charming apartment- lots of character. Plenty of space and good location. "
United States
Ashley
$105 nightly
The price is $126
Jan 11 - Jan 12
Total with taxes and fees
Goodramgate Apartments
Apartment | 2 bedrooms, Internet
Host Stay The Surfer s Loft Apartment

Host Stay The Surfer s Loft Apartment

Host Stay The Surfer s Loft Apartment
2.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (1 review)
$179 nightly
The price is $215
Jan 14 - Jan 15
Total with taxes and fees
Host Stay The Surfer s Loft Apartment
Fridge, microwave, oven, stovetop
Stoney Nook Cottage

Stoney Nook Cottage

Stoney Nook Cottage
Guisborough
9.2 out of 10, Wonderful, (5 reviews)
"Beautifully renovated cottage with comfortable bed and modern washroom. Conveniently located for exploring Guisborough and helpful guidebook with suggestions for the kids and adults. The grocery store is a 5-minute block away also. Andy was very helpful and easy to communicate with."
Canada
Shelley & J.
$118 nightly
The price is $118
Jan 18 - Jan 19
Total with taxes and fees
Stoney Nook Cottage
1 bedroom, desk, travel crib, bed sheets
Host & Stay | The Lobster Pot

Host & Stay | The Lobster Pot

Host & Stay | The Lobster Pot
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (1 review)
"Lovely location. Convenient for parking and travelling by bus. "
United States
Jessica J.
$145 nightly
The price is $145
Jan 11 - Jan 12
Total with taxes and fees
Host & Stay | The Lobster Pot
Exterior
Vas's York House

Vas's York House

Vas's York House
2.0 star property
Clifton
8.0 out of 10, Very Good, (2 reviews)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
$62 nightly
The price is $74
Jan 14 - Jan 15
Total with taxes and fees
Vas's York House
2 bedrooms, desk, iron/ironing board, travel crib
2 Bedroom House with Garden next to the River Tees

2 Bedroom House with Garden next to the River Tees

2 Bedroom House with Garden next to the River Tees
Stockton on Tees
10.0 out of 10, Exceptional, (2 reviews)
"Good location, host was very responsive, property had everything we needed. Good check-in/out process "
United Kingdom
David R.
$118 nightly
The price is $118
Jan 18 - Jan 19
Total with taxes and fees
2 Bedroom House with Garden next to the River Tees
Property grounds
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave

The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave

The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
High Leven
8.0 out of 10, Very Good, (13 reviews)
"Clean, well presented "
United Kingdom
Martin E.
$122 nightly
The price is $122
Jan 10 - Jan 11
Total with taxes and fees
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
Studio | Dining
Courtyard Rooms - Studio - Double Bed - Wifi

Courtyard Rooms - Studio - Double Bed - Wifi

Courtyard Rooms - Studio - Double Bed - Wifi
3.0 star property
Northallerton
8.0 out of 10, Very Good, (2 reviews)
"Very friendly reception from the landlord Gareth who provided a most enlivening atmosphere in the Duke of Wellington ie a darts match for the men and Easter wreath making for the ladies. No food unfortunately but we found an excellent Italian restaurant in nearby Northallerton. The courtyard room was clean and comfortable, marred only by a very awkward shower - not easy to enter, due to lack of space."
United Kingdom
Alison
$105 nightly
The price is $105
Jan 11 - Jan 12
Total with taxes and fees
Courtyard Rooms - Studio - Double Bed - Wifi
Smart TV
Entire house 🏠. suitable for families and workers.

Entire house 🏠. suitable for families and workers.

Entire house 🏠. suitable for families and workers.
Middlesbrough
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and a good area"
United Kingdom
Marek
$169 nightly
The price is $169
Jan 10 - Jan 11
Total with taxes and fees
Entire house 🏠. suitable for families and workers.
TV, fireplace
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Holgate
9.0 out of 10, Wonderful, (6 reviews)
"A great location for a weekend away in York. The property was spotless when we arrived and great communication from the owner. 25 minutes to walk into the centre of York, via the river path and free in street parking was a real bonus."
United Kingdom
Ian
$169 nightly
The price is $169
Jan 12 - Jan 13
Total with taxes and fees
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Helmsley Hotel Reviews

Moxy York

Moxy York

10/10 Excellent
"The room was lovely and clean. Staff were all friendly and helpful, even when we checked out the receptionist asked if there was anything else we would like help with. I thought this was a very thoughtful and nice thing to ask. The bar area was airy and well laid out and the drinks were reasonably priced."
Tracy 3-night trip
Posted 3 days ago
Moxy York

Find out more about Helmsley

Everything you need to know about Helmsley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Helmsley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Helmsley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Helmsley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Helmsley. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Helmsley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Helmsley rentals

At Expedia, we put the best Helmsley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Helmsley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Helmsley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Helmsley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Helmsley?

Yes, we give you a choice of vacation rentals close to well known local attractions in Helmsley, or you can select a secluded option if you want a relaxing place to stay. Visitors like the top-notch restaurants and spas in Helmsley. Make sure you have time to check out the parks while you're in the area.

What are some of the best vacation home rentals that Helmsley has to offer?

Vas's York House: Visitors like this Helmsley vacation home rental. It is equipped with a garden, daily housekeeping, and free WiFi to help you feel comfortable during your stay.

How many vacation rentals will I find in Helmsley?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Helmsley stay.

What can I see and do in Helmsley?

Howardian Hills and North York Moors National Park are a couple of scenic spots to enjoy the outdoors, whereas Helmsley Arts Centre is one of the cultural attractions. Other places in town to visit include Duncombe Park and Hemsley Walled Garden.

What are vacation rentals like in Helmsley?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Helmsley. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family gatherings.