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October Half Term in Whitby

With the fresh sea air, sandy beaches and lots of activities for the whole family to enjoy,

October Half Term is a lovely time to escape to Whitby.

We have a great selection of cottages and apartments available for October 2026, giving you the chance to find the

stay that suits you best. From family-friendly homes to dog-friendly coastal retreats, there’s something for everyone.

Why book now?

The widest range of properties and locations

Options for families, groups and couples

Dog-friendly stays so no one gets left behind

As demand builds, the most sought-after properties and dates are snapped up first.

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111

Abbey View (SC114)

9.6/10 - Rated "Fantastic"

Ideal for a solo traveller or couple seeking a peaceful countryside getaway that is within easy reach of Whitby and Scarborough.

 View & book
£400 ‐ £850
Sleeps 2
Bedrooms 1
1
1
111

Beach House (SC48)

9.4/10 - Rated "Fantastic"

Without doubt Beach House has some of the best sea and harbour views in Whitby. The setting could be straight from a picture postcard.

 View & book
£800 ‐ £2300
Sleeps 6
Bedrooms 3
2
2
111

Blackbird Cottage (SC112)

8.5/10 - Rated "Good"

A dog-friendly country cottage awash with mod cons and character. Ideal for couples or small families wanting walking or cycling breaks near Whitby.

 View & book
£550 ‐ £950
Sleeps 4
Bedrooms 2
1
111

Blue Horizon (SC117)

9.8/10 - Rated "Fantastic"

This stunning apartment enjoys views across Whitby’s West Cliff and out to sea which makes it so popular with guests.

 View & book
£500 ‐ £1200
Sleeps 4
Bedrooms 2
2
111

Boat Yard View (SC88)

8.5/10 - Rated "Very Good"

A spacious townhouse for up to eight guests within the modern Whitehall Landing development. Great location with parking and charming views over the boat yard.

 View & book
£550 ‐ £1800
Sleeps 8
Bedrooms 4
2
2
111

Captains Quarters (SC23)

9.0/10 - Rated "Excellent"

Magnificent harbour views and spacious accommodation sleeping up to eight guests in central Whitby – Captain’s Quarters is a real treasure!

 View & book
£750 ‐ £2200
Sleeps 8
Bedrooms 4
3
111

Carols Cottage (SC106)

9.5/10 - Rated "Excellent"

A two-bedroom apartment for four in the heart of the town on one of its most historic lanes – Flowergate

 View & book
£450 ‐ £950
Sleeps 4
Bedrooms 2
2
111

Chapel Cottage (SC92)

9.0/10 - Rated "Fantastic"

Family-friendly and dog-friendly, three bedroom character cottage with an enclosed garden in the peaceful and pretty village of Lythe, near Sandsend and Whitby.

 View & book
£665 ‐ £1450
Sleeps 6
Bedrooms 3
2
2
111

Chapel Gate Mews (SC80)

8.5/10 - Rated "Very Good"

A centrally located mews house for up to four guests and a dog. Book here for modern luxury, free parking and a garden.

 View & book
£580 ‐ £1250
Sleeps 4
Bedrooms 2
1
2
111

Cooks Cottage (SC40)

9.5/10 - Rated "Excellent"

A real gem that puts you close to Whitby Abbey on the East Side and has the best sea views!

 View & book
£450 ‐ £1200
Sleeps 4
Bedrooms 2
1
111

East Side View (SC95)

9.6/10 - Rated "Excellent"

Views do not get better than from this holiday property in Whitby! A great location for a romantic break, a small family or for two couples in the heart of the town

 View & book
£637.50 ‐ £1700
Sleeps 4
Bedrooms 2
1
111

Fossil Hunters (SC107)

9.3/10 - Rated "Excellent"

A four-bedroom, dog-friendly townhouse at the quieter end of Whitby’s east side. A modern, convenient and well-appointed holiday home with parking for two cars

 View & book
£500 ‐ £1500
Sleeps 6
Bedrooms 4
2
2
111

Hibwin House (SC100)

9.5/10 - Rated "Fantastic"

A 200-year-old, recently re-designed three-bedroom town house in central Whitby that’s an ideal holiday home for a small group or a family stay.

 View & book
£650 ‐ £1650
Sleeps 6
Bedrooms 3
3
1
111

Hoggarth House (SC110)

9.9/10 - Rated "Fantastic"

A luxury house in central Whitby that sleeps up to eight guests. Four bedrooms and four bathrooms. Beautifully furnished, tastefully styled and free parking onsite.

 View & book
£750 ‐ £1850
Sleeps 8
Bedrooms 4
4
1
111

Howdale Cottage (SC41)

8.5/10 - Rated "Very Good"

A dog-friendly cottage in a quaint village setting, close to Robin Hoods Bay. Private hot tub area for the ultimate romantic getaway.

 View & book
£450 ‐ £900
Sleeps 2
Bedrooms 1
1
111

Kipper Cottage (SC33)

8.5/10 - Rated "Very Good"

A fabulous sea-facing apartment for up to seven guests and a couple of dogs. The large, enclosed garden is a real Whitby gem.

 View & book
£600 ‐ £2400
Sleeps 7
Bedrooms 3
2
111

Low Tide Apartment (SC43)

8.9/10 - Rated "Very Good"

Great access to Whitby’s top attractions and a cosy retreat with river views. It’s a great choice for families with pets and cars.

 View & book
£400 ‐ £950
Sleeps 4
Bedrooms 2
1
1
111

Mariners Cottage (SC15)

8.8/10 - Rated "Very Good"

A newly refurbished, fisherman’s cottage in the centre of Whitby’s West Side. With free parking and three bedrooms, it’s perfect for families.

 View & book
£480 ‐ £1275
Sleeps 6
Bedrooms 3
2
1
111

Old Curiosity Shop (SC73)

9.0/10 - Rated "Excellent"

A remarkable, pet-friendly cottage for two that successfully combines history and contemporary comfort in the heart of Whitby.

 View & book
£400 ‐ £875
Sleeps 2
Bedrooms 1
1
111

Palmers (SC81)

10/10 - Rated "Fantastic"

A fabulous house between Staithes and Runswick Bay for groups of 8-12 guests. Packed with original and designer features for a luxurious stay.

 View & book
£950 ‐ £2250
Sleeps 8
Bedrooms 4
3
111

Pike Cottage (SC118)

9.2/10 - Rated "Excellent"

Nestled in the pretty village of Hinderwell, this holiday cottage near Staithes and Whitby is ideal for nature-lovers and those seeking a peaceful retreat.

 View & book
£375 ‐ £800
Sleeps 4
Bedrooms 2
1
1
111

Prince of Wales Cottage (SC69)

8.5/10 - Rated "Very Good"

A charming, recently refurbished traditional cottage that suits families looking for a central location for exploring the Abbey area with their dog.

 View & book
£450 ‐ £1250
Sleeps 6
Bedrooms 3
1
111

Quayside Cottage (SC9)

9.1/10 - Rated "Excellent"

A dog-friendly, quayside location where you can enjoy one of Yorkshire’s most historic towns, without compromising on your modern creature comforts.

 View & book
£400 ‐ £850
Sleeps 2
Bedrooms 1
1
111

Sandy Bottoms (SC119)

9.6/10 - Rated "Excellent"

A beautifully presented, pet-free holiday apartment in Whitby with parking and river views. A peaceful base with easy access to the main attractions and coastline.

 View & book
£500 ‐ £1280
Sleeps 6
Bedrooms 3
2
1
111

Solar Cottage (SC101)

9.1/10 - Rated "Excellent"

A unique, very secluded central Whitby location. Quirky and historic, warm and inviting. Our authentic fisherman’s cottage is a dream for 2-3 guests.

 View & book
£400 ‐ £950
Sleeps 3
Bedrooms 2
1
111

The Hideaway (SC121)

10/10 - Rated "Fantastic"

Luxury five-bedroom dog-friendly coastal retreat in central Whitby. Stylish, spacious and steps from the harbour front. Perfect for families or group getaways.

 View & book
£850 ‐ £1950
Sleeps 10
Bedrooms 5
3
111

The Landings (SC37)

9.4/10 - Rated "Excellent"

An exceptional, three-bedroom and dog-friendly townhouse. A leafy setting and a pleasant stroll to Whitbys old town await.

 View & book
£450 ‐ £1050
Sleeps 5
Bedrooms 3
3
1
111

The Olde Ship Inn (SC109)

9.9/10 - Rated "Fantastic"

A fabulous, dog-friendly duplex apartment in a former pub. Close to Whitbys heart, it’s a luxurious setting for six guests.

View & book
£650 ‐ £1650
Sleeps 6
Bedrooms 3
3
111

Tipple Cottage (SC53)

10/10 - Rated "Fantastic"

One of Whitby’s best cottages is packed with features and character. Superbly renovated, it provides free parking and sea view galore!

 View & book
£575 ‐ £1550
Sleeps 4
Bedrooms 2
2
1
111

Up the Creek Apartment (SC70)

8.5/10 - Rated "Very Good"

A ground floor riverside apartment in the perfect spot for exploring Whitby. Three bedrooms, dog friendly and with free parking right outside.

 View & book
£500 ‐ £1204
Sleeps 6
Bedrooms 3
2
1
111

Waters Edge Apartment (SC38)

9.1/10 - Rated "Excellent"

First-floor, wheelchair-friendly, modern apartment with lift and secure parking. Sleeps 5, river views and just 10 minutes to the Old Town.

 View & book
£450 ‐ £1100
Sleeps 5
Bedrooms 3
2
1
111

Whitby Sail Loft (SC122)

8.7/10 - Rated "Very Good"

Ground floor apartment on Whitehall Landing with open plan living, modern comforts and private parking, just a short stroll from the beach and town.

 View & book
£400 ‐ £950
Sleeps 4
Bedrooms 2
1
1
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Can’t find exactly what you’re looking for?

If you’d like to speak with us about your requirements, please give us a call. We're available Monday to Friday from 10am - 6pm. Our office is closed on a Saturday and Sunday but we check our answering service regularly so please leave a message and we’ll get back to you as soon as we can. 01947 668 888

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About Shoreline Whitby

We specialise in self-catering holidays, offering a selection of exceptional cottages, homes and apartments. Each property has been carefully chosen for its premium quality and stunning location. Since 1999 we've serviced over 27,500 holidays, so relax, you’re in experienced and trusted hands.

Read more about us

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'5 NIGHTS FOR THE PRICE OF 3'

On All Stays Taken Between

4 September - 30 October

BOOK TODAY
X

'5 NIGHTS FOR THE PRICE OF 3'

On All Stays Taken Between

4 September - 30 October

BOOK TODAY
X