A medieval castle surrounded by a lush green landscape and a small village in the background.

Helmsley Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Helmsley vacation rentals

Smart TV, offices

Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
The price is ￥75,742
￥85,737 total
includes taxes & fees
Jul 24 - Jul 25
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Cottage | Interior

29 Bondgate

29 Bondgate
3.5 star property
York
The price is ￥90,865
￥109,038 total
includes taxes & fees
Jul 23 - Jul 24
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
The price is ￥93,081
￥111,697 total
includes taxes & fees
Aug 13 - Aug 14
Cliff House
Room, Shared Bathroom (Dog Pod) | Exterior

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, (157 reviews)
"Everything was wonderful and amazing ill definetly be coming back "
United Kingdom
steffan
The price is ￥12,802
￥15,362 total
includes taxes & fees
Aug 2 - Aug 3
The Little Hide - Adult Only Camping Pods
Bar (on property)

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (43 reviews)
"The property was really clean and the staff really friendly and helpful and a credit to the comoany"
United Kingdom
Sharon
The price is ￥14,503
￥17,404 total
includes taxes & fees
Jul 31 - Aug 1
Station Suites
Superior Room, 1 Double Bed (Double Studio) | 1 bedroom, in-room safe, desk, iron/ironing board

CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.8 out of 10, Excellent, (9 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is ￥11,948
￥15,173 total
includes taxes & fees
Jul 19 - Jul 20
CoStays Aparthotel - Middlesbrough
Interior

Cosy Rural Cabin with Private Hot Tub

Cosy Rural Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (8 reviews)
"Lovely pods, great area, nice and safe for the kids, everything provided, owners took us to feed the animals, bbq a great bonus"
United States
Alex
The price is ￥43,114
￥43,114 total
includes taxes & fees
Jul 19 - Jul 20
Cosy Rural Cabin with Private Hot Tub
Exterior

Baby Moon

Baby Moon
2.0 star property
Guisborough
9.6 out of 10, Exceptional, (10 reviews)
"Really good customer service, the yurt was very comfortable. Good sites nearby to drive to (not walking distance)."
United Kingdom
Anonymous traveler
The price is ￥24,736
￥24,736 total
includes taxes & fees
Jul 19 - Jul 20
Baby Moon
Studio | Dining

Welbury Studio Retreat

Welbury Studio Retreat
3.0 star property
Northallerton
9.4 out of 10, Exceptional, (3 reviews)
"Very helpful, we were going to be later than anticipated arriving, phoned to let them know, they reassured us it was no problem, everything was ready for our stay. Check-in at the bar was easy, staff showed us to our studio, staff very cheerful. Food in the pub was great, not just pub grub. Only downside, studio was small."
United Kingdom
Gillian
The price is ￥9,551
￥11,462 total
includes taxes & fees
Jul 19 - Jul 20
Welbury Studio Retreat
Exterior

Old Mill Tiny Homes

Old Mill Tiny Homes
2.0 star property
Yarm
10.0 out of 10, Exceptional, (1 review)
"Spotlessly clean and so cosy Brilliant stay Lovely pub within walking distance "
United Kingdom
Caroline
The price is ￥27,149
￥32,578 total
includes taxes & fees
Jul 28 - Jul 29
Old Mill Tiny Homes
Interior

Pippin Cottage

Pippin Cottage
3.0 star property
Ripon
The price is ￥55,590
￥66,708 total
includes taxes & fees
Aug 12 - Aug 13
Pippin Cottage
Exterior

Glamping Pod in Yorkshire Wolds near York

Glamping Pod in Yorkshire Wolds near York
York
9.4 out of 10, Exceptional, (48 reviews)
"The kitchen setup was well thought out, We made several meals during our stay and found everything we needed,"
United States
Anonymous traveler
The price is ￥64,596
￥64,596 total
includes taxes & fees
Jul 21 - Jul 22
Glamping Pod in Yorkshire Wolds near York
Outdoor dining

The Byre is in Great Broughton

The Byre is in Great Broughton
Middlesbrough
The price is ￥64,770
￥64,770 total
includes taxes & fees
Jul 19 - Jul 20
The Byre is in Great Broughton
Exterior

Glamping Pod in Yorkshire Wolds Countryside

Glamping Pod in Yorkshire Wolds Countryside
York
9.8 out of 10, Exceptional, (25 reviews)
"The private seating area outside was wonderful for evening barbecues, We rented a gas grill and spent our nights enjoying the fresh air,"
United States
Anonymous traveler
The price is ￥64,681
￥64,681 total
includes taxes & fees
Jul 21 - Jul 22
Glamping Pod in Yorkshire Wolds Countryside
2 bedrooms, iron/ironing board, travel crib, WiFi (free)

Boutique Barn Secure Parking between York & Harrogate

Boutique Barn Secure Parking between York & Harrogate
York, North Yorkshire
10.0 out of 10, Exceptional, (2 reviews)
"Lovely stay at the Barn in Whixley. The barn was immaculately clean, had a fabulous layout with bedrooms downstairs very modern but with character. Michelle the host was very friendly and informative. The barn is very well located, would defiantly recommend and would return again."
United States
Jacqui B.
Boutique Barn Secure Parking between York & Harrogate
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
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.
The price is ￥15,644
￥19,120 total
includes taxes & fees
Jul 27 - Jul 28
2 Bedroom House with Garden next to the River Tees
Living area

Beautiful riverside apartment in the heart of Thirsk

Beautiful riverside apartment in the heart of Thirsk
Thirsk
The price is ￥23,857
￥27,333 total
includes taxes & fees
Jul 27 - Jul 28
Beautiful riverside apartment in the heart of Thirsk
Exterior

The Cottage, Thornton Dale

The Cottage, Thornton Dale
Pickering
The price is ￥78,252
￥78,252 total
includes taxes & fees
Jul 27 - Jul 28
The Cottage, Thornton Dale
Interior

Manor House Farm Cottage, Staithes

Manor House Farm Cottage, Staithes
Saltburn-by-the-Sea
The price is ￥73,689
￥73,689 total
includes taxes & fees
Jul 18 - Jul 19
Manor House Farm Cottage, Staithes
House | 1 bedroom

Host Stay The Lobster Pot

Host Stay The Lobster Pot
2.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (2 reviews)
"Great 1 night stay, very friendly host, spotlessly clean. Great location only a few minutes walk to nearest pub. "
United Kingdom
Vicky
The price is ￥22,332
￥29,632 total
includes taxes & fees
Jul 19 - Jul 20
Host Stay The Lobster Pot
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

Mercure York Fairfield Manor Hotel

Mercure York Fairfield Manor Hotel

8/10 Good
"Nice location and reasonable rooms for the money. No air conditioning in the rooms made them unbearable. There was a fan (seemingly from the 70's) but only 2 plug sockets in the room, neither if which near the bed, so the fan had no affect whatsoever. Staff we friendly and helpful but food and drinks weren't great quality and were massively overpriced"
Lloyd 2-night trip
Posted 14 hours ago
Mercure York Fairfield Manor Hotel

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia! You can easily find your home rentals, villas, holiday apartments in Helmsley using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Helmsley?

Yes, we give you a choice of vacation rentals in Helmsley close to Helmsley Arts Centre, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 7 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 Helmsley Castle 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.