Estia Villas - Vacation Rentals in Helmsley
Cottage
9.0
(
2 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking -
Balcony/Terrace -
Kitchen -
Internet
US $496
/Night
7 Nights - $3,471
House
10.0
(
2 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1399.31 ft²
-
Parking
-
View -
Internet
-
Child Friendly
US $312
/Night
7 Nights - $2,186
Bed & Breakfast
9.8
(
20 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Balcony/Terrace
-
Internet
US $183
/Night
7 Nights - $1,281
Cottage
9.2
(
15 Reviews
)
2 Bedrooms
3 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Child Friendly
US $87
/Night
7 Nights - $611
House
10.0
(
82 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Ocean View -
Balcony/Terrace
-
View
US $300
/Night
7 Nights - $2,103
House
10.0
(
60 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $297
/Night
7 Nights - $2,078
Cottage
10.0
(
12 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $168
/Night
7 Nights - $1,175
Cottage
10.0
(
3 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $335
/Night
7 Nights - $2,344
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Luxury Places to Stay in Helmsley
Over 107+
Luxury Places to Stay in or Near Helmsley
House
9.2
(
7 Reviews
)
7 Bedrooms
5 Bathrooms
20 Guests
3692.02 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Internet
US $1,442
/Night
7 Nights - $10,094
New
Cottage
2 Bedrooms
1 Bathroom
4 Guests
1292 ft²
-
Kitchen
-
Internet
-
Bedding/Linens -
Security/Safety
US $1,214
/Night
7 Nights - $8,495
House
8.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $1,210
/Night
7 Nights - $8,473
Cottage
4 Bedrooms
4 Bathrooms
8 Guests
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $989
/Night
7 Nights - $6,923
House
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
View
-
Internet
-
Pet Friendly
US $950
/Night
7 Nights - $6,653
House
8.6
(
11 Reviews
)
5 Bedrooms
4 Bathrooms
13 Guests
2002.09 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Internet
US $828
/Night
7 Nights - $5,797
New
Cottage
2 Bedrooms
3 Bathrooms
4 Guests
-
Hot Tub
-
Parking
-
Spa -
Balcony/Terrace
US $824
/Night
7 Nights - $5,766
US $798
/Night
7 Nights - $5,585
See More Helmsley Luxury Vacation Rentals
Find More Helmsley Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Helmsley
Over 3+
Top-Rated Vacation Rentals with a Pool in or Near Helmsley
US $222
/Night
7 Nights - $1,556
Hotel
8.6
(
661 Reviews
)
282.56 ft²
-
Oceanfront -
Hot Tub
-
Breakfast
-
EV Charge Station
US $200
/Night
7 Nights - $1,402
Cottage
3 Bedrooms
1 Bathroom
6 Guests
1399 ft²
-
Pool -
Balcony/Terrace
-
Kitchen
-
Internet
US $700
/Night
7 Nights - $4,903
Pet-Friendly Vacation Rentals in Helmsley
Over 65+
Pet-Friendly Vacation Rentals in or Near Helmsley
Apartment
10.0
(
1 Review
)
1 Bedroom
3 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $567
/Night
7 Nights - $3,967
House
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
161.46 ft²
-
EV Charge Station
-
Parking
-
Balcony/Terrace
-
View
US $158
/Night
7 Nights - $1,109
US $677
/Night
7 Nights - $4,739
Cottage
9.6
(
5 Reviews
)
3 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $210
/Night
7 Nights - $1,472
Cottage
9.6
(
4 Reviews
)
3 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $170
/Night
7 Nights - $1,189
Cottage
9.6
(
4 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $65
/Night
7 Nights - $452
Cottage
9.4
(
3 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $307
/Night
7 Nights - $2,146
Cottage
9.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $372
/Night
7 Nights - $2,607
See More Pet-Friendly Vacation Rentals in Helmsley on PetFriendly.io
Large Vacation Homes & Villas in Helmsley
Over 5+
Large Vacation Homes & Villas in or Near Helmsley
Cottage
5 Bedrooms
3 Bathrooms
10 Guests
2153 ft²
-
Kitchen
-
Internet
-
Pet Friendly
-
Child Friendly
US $775
/Night
7 Nights - $5,426
House
8.2
(
22 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
2002.09 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Internet
US $614
/Night
7 Nights - $4,298
Cottage
10.0
(
1 Review
)
5 Bedrooms
6 Bathrooms
14 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $890
/Night
7 Nights - $6,231
Apartment
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
10 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $626
/Night
7 Nights - $4,382
Cottage
7 Bedrooms
7 Bathrooms
20 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,287
/Night
7 Nights - $9,009
See More Family Vacation Rentals in Helmsley on FVR
Wheelchair Accessible Vacation Homes in Helmsley
Over 1+
Wheelchair Accessible Vacation Homes in or Near Helmsley
Hotel
8.7
(
1395 Reviews
)
135.32 ft²
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Internet
US $119
/Night
7 Nights - $831
Helmsley Vacation Rentals and Airbnb Places to Stay Under $200
Over 20+
Helmsley Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
10.0
(
2 Reviews
)
3 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $154
/Night
7 Nights - $1,079
Bed & Breakfast
9.5
(
92 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
365.97 ft²
-
Parking
-
Internet
-
Security/Safety
US $168
/Night
7 Nights - $1,179
Hotel
9.4
(
499 Reviews
)
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $120
/Night
7 Nights - $840
Cottage
9.4
(
14 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Pet Friendly
US $196
/Night
7 Nights - $1,374
Cottage
9.8
(
10 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $131
/Night
7 Nights - $914
Cottage
9.6
(
10 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $139
/Night
7 Nights - $972
Cottage
9.2
(
5 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $127
/Night
7 Nights - $890
US $171
/Night
7 Nights - $1,195
See More Helmsley Vacation Rental Deals
Instantly Bookable Vacation Homes in Helmsley
Over 30+
Instantly Bookable Vacation Homes in or Near Helmsley
House
10.0
(
2 Reviews
)
3 Bedrooms
1 Bathroom
5 Guests
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Child Friendly
US $604
/Night
7 Nights - $4,225
Cottage
8.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $369
/Night
7 Nights - $2,584
Cottage
4 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $691
/Night
7 Nights - $4,838
New
Cottage
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $679
/Night
7 Nights - $4,751
Cottage
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $631
/Night
7 Nights - $4,420
Cottage
4 Bedrooms
2 Bathrooms
8 Guests
1938 ft²
-
Kitchen
-
Internet
-
Pet Friendly
-
Child Friendly
US $616
/Night
7 Nights - $4,311
Cottage
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $540
/Night
7 Nights - $3,779
House
1 Bedroom
1 Bathroom
2 Guests
646 ft²
-
Kitchen
-
Internet
-
Pet Friendly
-
Laundry
US $531
/Night
7 Nights - $3,718
See More Helmsley Short-Term Vacation Rentals
About Helmsley Vacation Rentals
With more than 116 Helmsley vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Helmsley.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Helmsley, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Helmsley. Places to stay near Helmsley are 358.79 ft² on average, with prices averaging US $401 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Helmsley with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Helmsley
| Type | Count |
|---|---|
| Cottages | 54 |
| Vacation Homes | 45 |
| Hotels | 7 |
| Holiday Apartments | 5 |
| B&B | 3 |
| Hostels | 1 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Helmsley
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Helmsley.
Weather in Helmsley
View the weather forecast for Helmsley before booking your Helmsley Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 32°F
March - May
High 61°F Low 36°F
June - August
High 63°F Low 48°F
September - November
High 58°F Low 35°F
Top Attractions Around Helmsley, GB
Estiavillas offers a large selection of top attractions around Helmsley. Research things to do on your vacation before you visit Helmsley.
Hemsley Walled Garden
Helmsley Arts Centre
Duncombe Park
Helmsley Castle
Flamingo Land Theme Park and Zoo
North York Moors National Park
Castle Howard
Dalby Forest Visitor Centre
Eden Camp Modern History Theme Museum
Danby Castle
York Hospital
World of James Herriot
Yorkshire Lavender
North Riding Forest Park
Rievaulx Abbey
Yorkshire Arboretum
North Yorkshire Moors Railway
Aldwark Manor Spa
Rosedale Abbey
Pickering Castle
Other Places to Stay Near Helmsley, GB
Complexes around Helmsley, GB
Helmsley Vacation Rental Frequently Asked Questions
Which vacation homes in Helmsley are best for families?
If you are looking for a family-friendly vacation home in Helmsley, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Helmsley:
How many vacation rentals are available in Helmsley?
Currently, the total number of properties listed in 2026 is over 116 in the Helmsley area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Helmsley.
