Holiday rentals near Cleveland Way

We found 2,182 holiday rentals — enter your dates for availability

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February 2026

March 2026

Choose the perfect holiday rental within easy reach of Cleveland Way. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as parking and a TV. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Cleveland Way

Showing deals for:8 May - 15 May

Silton Hall, Nether Silton - Host & Stay

Very good

(6 reviews)

Host & Stay | Silton Hall

Northallerton

19% off

for 7 nights, 1 home

AU$1,189 per night

includes taxes & fees

Exceptional

(11 reviews)

The Cottage Gillamoor York, with wood burner, wifi and good local pub

Gillamoor

36% off

for 7 nights, 1 cottage

AU$268 per night

includes taxes & fees

Very good

(6 reviews)

The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite

High Leven

12% off

for 7 nights, 1 cottage

AU$310 per night

includes taxes & fees

Exceptional

(40 reviews)

Central Whitby Townhouse sleeping 12 people with private parking

Whitby

38% off

for 7 nights, 1 home

AU$589 per night

includes taxes & fees

Exceptional

(52 reviews)

Gulls Cry Cottage 17th Century Detached Cottage 2min's from Harbour Side

Whitby

28% off

for 7 nights, 1 cottage

AU$325 per night

includes taxes & fees

Exceptional

(93 reviews)

Central 5 bed/3 bath for 8 (+ cot) free parking - spacious, stylish, comfortable

Whitby

8% off

for 7 nights, 1 home

AU$584 per night

includes taxes & fees

Garth End Cottage showing site on the sea wall

Exceptional

(84 reviews)

Characterful Georgian Cottage On Harbour Front With Wonderful Sea Views

Staithes

33% off

for 7 nights, 1 cottage

AU$172 per night

includes taxes & fees

Exceptional

(135 reviews)

Cottage in the centre of Whitby - beautiful coastal and Abbey views

Whitby

11% off

for 7 nights, 1 home

AU$236 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cleveland Way

CHAPEL COTTAGE, pet friendly, with open fire in Saltburn-By-The-Sea

3 bedrooms · 1 bathroom

Top rated rentals - Cleveland Way

Image of ⭐️EXCEPTIONAL ONE BEDROOM APARTMENT WHITBY -ABBEY VIEWS & 3PM CHECK IN SLEEPS 4

Premier Host

Perfect

The apartment is perfectly locaated within easy walking distance of the main attractions. We booked a short stay and were super comfortable.Communication was very easy Would highly recommend

Kevin F.

Stayed Aug 2025

Image of 2 Bedroom House with Garden next to the River Tees

Good stopover to break up a long drive.

The house was spacious and suited our needs. A deeper clean is probably due, especially in the kitchen.

Susan C.

Stayed June 2024

Premier Host

Oystercatcher, Whitby is perfect for a couple.

We loved everything about the apartment and the location is perfect. We spent 2 weeks there and it really felt like home to us - so far from our Australian home!! Whitby has so much to do and the regatta was an added bonus! Have sent the link for Oystercatcher Apartment to our friends!

Nonnie M.

Stayed Aug 2023

Image of Situated in the heart of the village, within metres of the sea and sandy beach.

A beautiful cottage in a glorious location!

The attention to detail in the cottage is impeccable. We found everything we needed and the view and welcome were amazing. Sarah was very responsive and we loved our cake and Prosecco on arrival. We will highly recommend this to our friends and family. And hopefully be back ourselves!

Kate W.

Stayed Oct 2018

Peace of mind
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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
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