Holiday rentals near Cleveland Way

We found 1,926 holiday rentals — enter your dates for availability

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November 2025

December 2025

Find the perfect private holiday rental that's close to Cleveland Way. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Cleveland Way

Showing deals for:30 Jan - 6 Feb

Exceptional

(7 reviews)

Meadowside House @ The Bay Filey, Pool, Beach Access

Filey, England

14% off

for 7 nights, 1 cottage

NZ$851 per night

includes taxes & fees

Rear of Beach Haven Cottage with BBQ and South facing patio.

Exceptional

(252 reviews)

Filey. Active leisure or relaxing beach holiday.

Filey, ENG

9% off

for 7 nights, 1 cottage

NZ$240 per night

includes taxes & fees

Exceptional

(49 reviews)

Harlequin dog friendly 2 bedroomed cottage at The Bay with access to the beach

Filey, ENG

13% off

for 7 nights, 1 cottage

NZ$222 per night

includes taxes & fees

Exceptional

(175 reviews)

Lavender Cottage, WiFi, holiday complex, Leisure facilities, direct beach access

Hunmanby, ENG

10% off

for 7 nights, 1 cottage

NZ$400 per night

includes taxes & fees

Exceptional

(13 reviews)

Chalk Cottage at Flamborough, Yorkshire Coast, Four Star Accomodation. Sleeps 5

Bridlington, ENG

10% off

for 7 nights, 1 cottage

NZ$319 per night

includes taxes & fees

Very good

(6 reviews)

Beam End Snainton - Modern 2-bedroom Stone Cottage. Pet Friendly.

Scarborough, North Yorkshire

13% off

for 7 nights, 1 cottage

NZ$247 per night

includes taxes & fees

Exceptional

(15 reviews)

Endways Cottage 18th Century Cottage. Sleeps 6 in 3 bedrooms with 2 bathrooms.

Whitby, England

18% off

for 7 nights, 1 cottage

NZ$278 per night

includes taxes & fees

Rear of the cottage from the boules pitch, showing Beach Haven Cottage near RHS.

Exceptional

(270 reviews)

Filey. Active leisure or relaxing beach holiday.

Filey, ENG

9% off

for 7 nights, 1 cottage

NZ$240 per night

includes taxes & fees

The Old Jail Barber's, Seamer - Host & Stay

Exceptional

(5 reviews)

Host & Stay | The Old Jail Barber's Shop

Scarborough, England

14% off

for 7 nights, 1 home

NZ$270 per night

includes taxes & fees

Exceptional

(55 reviews)

Sea View Mews, Reighton near Filey - a rural cottage with uninterrupted sea view

Filey

14% off

for 7 nights, 1 cottage

NZ$281 per night

includes taxes & fees

Mill Farm Filey Cottages entrance - Filey View Cottage is on the right hand side

Exceptional

(56 reviews)

LOVELY PEACEFUL COTTAGE SLEEPS 4 | CLOSE TO FILEY TOWN & BEACH | GARDEN

Filey, ENG

37% off

for 7 nights, 1 cottage

NZ$141 per night

includes taxes & fees

Exceptional

(17 reviews)

The Old Forge, 4 Bed Modern Barn Conversion in The Yorkshire Wolds

Malton, North Yorkshire

31% off

for 7 nights, 1 home

NZ$466 per night

includes taxes & fees

Exceptional

(102 reviews)

Pretty Seaside cottage, sleeps 4 ( dog friendly )

Bridlington, England

5% off

for 7 nights, 1 cottage

NZ$344 per night

includes taxes & fees

Front of the cottage, showing driveway parking.

Exceptional

(123 reviews)

Flamborough Cottage large private garden parking, pets welcome.<br>Wifi .

Bridlington, ENG

22% off

for 7 nights, 1 cottage

NZ$198 per night

includes taxes & fees

Othala @ The Merchants Quarters, Scarborough - Host & Stay

Exceptional

(5 reviews)

Host & Stay | Othala @ The Merchants Quarters

Scarborough, England

14% off

for 7 nights, 1 apartment

NZ$236 per night

includes taxes & fees

Exceptional

(36 reviews)

Elegant Townhouse, Sleeps 12, Close beach/town, 4 bath/showers, Sky Sports

Scarborough

37% off

for 7 nights, 1 home

NZ$492 per night

includes taxes & fees

Exceptional

(7 reviews)

17th Century cottage in the heart of smugglers fishing village.

Whitby

18% off

for 7 nights, 1 cottage

NZ$263 per night

includes taxes & fees

Boutique fisherman's cottage in heart Old Town Scarborough with private parking

Exceptional

(26 reviews)

Unique Fisherman's Cottage Old Town Scarborough, private parking, enc garden.

Scarborough, England

8% off

for 7 nights, 1 home

NZ$426 per night

includes taxes & fees

Decking and bifold doors to bring the outside in.

Exceptional

(140 reviews)

Beaurepaire, Beach House at The Bay Filey.

Filey, ENG

5% off

for 7 nights, 1 home

NZ$271 per night

includes taxes & fees

Exceptional

(11 reviews)

Ground Floor Beachfront Apartment, Amazing Views

Bridlington, East Riding of Yorkshire

14% off

for 7 nights, 1 apartment

NZ$284 per night

includes taxes & fees

Exceptional

(5 reviews)

Host & Stay | Wicket View @ North Marine House

Scarborough, England

13% off

for 7 nights, 1 apartment

NZ$141 per night

includes taxes & fees

Exceptional

(6 reviews)

No Pets ! The Belvedere Apartment short walk to the beach, spa and town

Scarborough, ENG

18% off

for 7 nights, 1 apartment

NZ$298 per night

includes taxes & fees

No 53 is a 2 bedroom town house. You have the whole house to yourselves

Exceptional

(9 reviews)

Scarborough Central Pet friendly House - Perfect for couples- WIFI-Free Parking

Scarborough, England

18% off

for 7 nights, 1 home

NZ$182 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Cleveland Way

Premier Host

40ft x 20ft luxury holiday lodge near Scarborough; 3 bed, sleeps 6, hot tub

Sleeps 6 · 3 bedrooms · 2 bathrooms

Premier Host

Beach House "Just Beachy" Pool, Gym, Pet Friendly, close to Beach, WiFi, Netflix

Sleeps 4 · 2 bedrooms · 2 bathrooms

Filey-Ground Floor Apartment, Sea View, Private patio. Dog friendly (maximum 2).

Sleeps 6 · 3 bedrooms · 2 bathrooms

Premier Host

Dog friendly cottage, town centre, close to the beach, WI-FI & parking included.

Sleeps 4 · 2 bedrooms · 1 bathroom

LOVELY PEACEFUL COTTAGE SLEEPS 4 | CLOSE TO FILEY TOWN & BEACH | GARDEN

Sleeps 4 · 2 bedrooms · 2 bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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