Holiday rentals near Cleveland Way
We found 2,092 holiday rentals — enter your dates for availability
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:14 Nov - 21 Nov
Image gallery for The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
8.08.0 out of 10 rating
Very good
(13 reviews)
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
Yarm, England
9% off
Price is AU$1,079
AU$1,079
AU$154 per night
includes taxes & fees
Image gallery for Easily accessible, single level, 3-bed cottage close to beach, shops & eateries!
9.29.2 out of 10 rating
Wonderful
(13 reviews)
Easily accessible, single level, 3-bed cottage close to beach, shops & eateries!
Saltburn-by-the-Sea, England
19% off
Price is AU$1,843
AU$1,843
AU$263 per night
includes taxes & fees
Image gallery for Family friendly holiday cottage in the beautiful North Yorkshire countryside.
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Family friendly holiday cottage in the beautiful North Yorkshire countryside.
Middlesbrough, North Yorkshire
17% off
Price is AU$2,339
AU$2,339
AU$334 per night
includes taxes & fees
Image gallery for Large Family-Friendly Cottage Near Whitby – Sleeps 10, Perfect for Groups
1010 out of 10 rating
Exceptional
(15 reviews)
Large Family-Friendly Cottage Near Whitby – Sleeps 10, Perfect for Groups
Whitby, York & North Yorkshire
38% off
Price is AU$3,692
AU$3,692
AU$527 per night
includes taxes & fees
Image gallery for No. 10 West End Osmotherley
9.69.6 out of 10 rating
Exceptional
(41 reviews)
No. 10 West End Osmotherley
Northallerton, ENG
9% off
Price is AU$1,998
AU$1,998
AU$285 per night
includes taxes & fees
Image gallery for Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
9.89.8 out of 10 rating
Exceptional
(277 reviews)
Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
Whitby, ENG
5% off
Price is AU$1,128
AU$1,128
AU$161 per night
includes taxes & fees
Image gallery for Host & Stay | Simba House
1010 out of 10 rating
Exceptional
(5 reviews)
Host & Stay | Simba House
Saltburn-by-the-Sea, England
14% off
Price is AU$2,330
AU$2,330
AU$333 per night
includes taxes & fees
Image gallery for A 200 year old, delightful, fisherman's cottage, ideally located in Whitby.
9.89.8 out of 10 rating
Exceptional
(24 reviews)
A 200 year old, delightful, fisherman's cottage, ideally located in Whitby.
Whitby, England
9% off
Price is AU$2,022
AU$2,022
AU$289 per night
includes taxes & fees
Image gallery for Beautifully refurbished cottage in the heart of Staithes - with stunning views
9.69.6 out of 10 rating
Exceptional
(26 reviews)
Beautifully refurbished cottage in the heart of Staithes - with stunning views
Saltburn-by-the-Sea, ENG
9% off
Price is AU$3,066
AU$3,066
AU$438 per night
includes taxes & fees
Image gallery for Luxury Cottage for two
1010 out of 10 rating
Exceptional
(41 reviews)
Luxury Cottage for two
Whitby
9% off
Price is AU$1,929
AU$1,929
AU$276 per night
includes taxes & fees
Image gallery for Riverside Cottage, Whitby, overlooking the River Esk
8.68.6 out of 10 rating
Excellent
(22 reviews)
Riverside Cottage, Whitby, overlooking the River Esk
Whitby, ENG
38% off
Price is AU$1,464
AU$1,464
AU$209 per night
includes taxes & fees
Image gallery for Central Whitby Townhouse sleeping 12 people with private parking
1010 out of 10 rating
Exceptional
(39 reviews)
Central Whitby Townhouse sleeping 12 people with private parking
Whitby
38% off
Price is AU$3,181
AU$3,181
AU$454 per night
includes taxes & fees
Image gallery for Luxury Romantic Cottage for two
1010 out of 10 rating
Exceptional
(62 reviews)
Luxury Romantic Cottage for two
Whitby, ENG
9% off
Price is AU$1,929
AU$1,929
AU$276 per night
includes taxes & fees
Image gallery for Luxury Detached Home Overlooking The North Yorkshire Moors
1010 out of 10 rating
Exceptional
(40 reviews)
Luxury Detached Home Overlooking The North Yorkshire Moors
Whitby, North Yorkshire
23% off
Price is AU$3,920
AU$3,920
AU$560 per night
includes taxes & fees
Image gallery for Meadows Edge Cottage, Dog/Cat Friendly with fishing on site
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Meadows Edge Cottage, Dog/Cat Friendly with fishing on site
Pickering, England
5% off
Price is AU$2,739
AU$2,739
AU$391 per night
includes taxes & fees
Image gallery for Cottage in idyllic setting, a short drive from Staithes
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Cottage in idyllic setting, a short drive from Staithes
Saltburn-by-the-Sea, England
14% off
Price is AU$1,756
AU$1,756
AU$251 per night
includes taxes & fees
Image gallery for Host & Stay | Artsbank Apartment
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Host & Stay | Artsbank Apartment
Saltburn-by-the-Sea, England
14% off
Price is AU$1,221
AU$1,221
AU$174 per night
includes taxes & fees
Image gallery for Top Gallant Holiday Cottage Runswick Bay with great beach and sea views
1010 out of 10 rating
Exceptional
(105 reviews)
Top Gallant Holiday Cottage Runswick Bay with great beach and sea views
Saltburn-by-the-Sea, N Yorkshire
5% off
Price is AU$2,109
AU$2,109
AU$301 per night
includes taxes & fees
Image gallery for Host & Stay | Retreat By The Sea
8.68.6 out of 10 rating
Excellent
(10 reviews)
Host & Stay | Retreat By The Sea
Redcar, England
14% off
Price is AU$1,295
AU$1,295
AU$185 per night
includes taxes & fees
Image gallery for Host & Stay | Gun Gutter House
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Host & Stay | Gun Gutter House
Saltburn-by-the-Sea, England
14% off
Price is AU$1,567
AU$1,567
AU$224 per night
includes taxes & fees
Image gallery for Stunning Country Cottage set within the North Yorks Moors National Park
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Stunning Country Cottage set within the North Yorks Moors National Park
Whitby, England
9% off
Price is AU$6,111
AU$6,111
AU$873 per night
includes taxes & fees
Image gallery for Host & Stay | Simon Howe Lodge
1010 out of 10 rating
Exceptional
(5 reviews)
Host & Stay | Simon Howe Lodge
Whitby, England
14% off
Price is AU$2,243
AU$2,243
AU$320 per night
includes taxes & fees
Image gallery for Host & Stay | Princes Road
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Host & Stay | Princes Road
Saltburn-by-the-Sea, England
14% off
Price is AU$2,395
AU$2,395
AU$342 per night
includes taxes & fees
Image gallery for Cosy Beachside Apartment, Spectacular Views in Picturesque Village.
8.48.4 out of 10 rating
Very good
(6 reviews)
Cosy Beachside Apartment, Spectacular Views in Picturesque Village.
Whitby, England
19% off
Price is AU$2,216
AU$2,216
AU$317 per night
includes taxes & fees
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Find the best place to stay - Cleveland Way
Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
Sleeps 2 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
277 reviews(277 reviews)
Situated in the heart of the village, within metres of the sea and sandy beach.
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
170 reviews(170 reviews)
Two double bedroom flat with fantastic roof terrace overlooking Swing Brid
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
148 reviews(148 reviews)
Spectacular Waterfront Location with Balcony
Sleeps 3 · 2 bedrooms
9.69.6 out of 10
Exceptionalexceptional
85 reviews(85 reviews)
There Is An Indoor Swimming Pool For The Use Of Visitors To The Site Only
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
Cottage in the centre of Whitby - beautiful coastal and Abbey views
Sleeps 6 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
123 reviews(123 reviews)
Top rated rentals - Cleveland Way
Perfect
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
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
Oystercatcher, Whitby is perfect for a couple.
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
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
Excellent
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Very comfortable and quiet.
Trish J.
Stayed Sept 2022
A beautiful cottage in a glorious location!
1010 out of 10
Exceptionalexceptional
170 reviews(170 reviews)
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 mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value