Pickering Holiday Homes

Choose from 46 holiday homes in Pickering - from cosy cottages near North York Moors Railway to lodges with indoor pools. Check rates and book now.

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1-20 out of 48
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  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
9.5
Perfect530 total reviews
our site & Booking.com
6 adults
3 bedrooms
3 beds
FishingGolf CourseChildren's Playground
  • 18th-century farmhouse on 16 acres
  • Self-catering cottages by river
  • On-site fishing and golf course
From£ 170 /nightSelect
Low Costa MillHoliday home
9.8
Perfect25 total reviews
our site & Booking.com
6 adults
3 bedrooms
3 beds
Map
2.0 km from City Centre
Private PoolEV ChargingChildren's Playground
  • Private heated indoor pool
  • Electric vehicle charging station
  • On-site fishing activities
From£ 199 /nightSelect
9.7
Perfect70 total reviews
our site & Booking.com
4 adults
2 bedrooms
2 beds
Map
2.4 km from City Centre2.2 km from Pickering Castle
Hot TubFull KitchenPS4 Console
  • Private hot tub in chalet
  • PS4 and fully equipped kitchen
  • Garden views and private patio
From£ 212 /nightSelect
Hogwarts CottageHoliday home
7.8
Very good38 total reviews
our site & Booking.com
4 adults
2 bedrooms
2 beds
Map
300 m from City Centre100 m from North Yorkshire Moors Railway
Private GardenWashing MachineGolf Course
  • On-site golf course
  • Pet-friendly garden cottage
  • On-site fishing and cycling
From£ 169 /nightSelect
9.3
Perfect73 total reviews
our site & Booking.com
Map
300 m from City Centre600 m from North Yorkshire Moors Railway
GardenTerracePrivate Entrance
  • 300-year-old historic cottage
  • Garden with patio views
  • Private entrance and fireplace
From£ 166 /nightSelect
9.0
Perfect2 total reviews
our site & Booking.com
10 adults
5 bedrooms
2 beds
Map
500 m from City Centre300 m from Green Man Gallery
Children's PlaygroundPrivate ParkingFireplace
  • On-site children's playground
  • Cozy fireplace in living area
  • Pets allowed on request
From£ 196 /nightSelect
Potter Hill CottageHoliday home
9.7
Perfect51 total reviews
our site & Booking.com
5 adults
3 bedrooms
3 beds
Map
100 m from City Centre300 m from Green Man Gallery
FireplaceFull KitchenWalk-in Shower
  • Spacious cottage with fireplace
  • On-site cycling, fishing, golf
  • Near Flamingo Land Theme Park
From£ 367 /nightSelect
Cobbler'S CottageHoliday home
7.6
Very good6 total reviews
our site & Booking.com
5 adults
3 bedrooms
3 beds
Map
800 m from City Centre600 m from Green Man Gallery
Pet FriendlyFireplaceWalk-In Shower
  • Pet-friendly holiday home
  • Self-catering with fireplace
  • Near Flamingo Land
From£ 614 /nightSelect
Keep CottageHoliday home
10.0
Perfect1 total review
our site & Booking.com
5 adults
3 bedrooms
3 beds
Map
500 m from City Centre100 m from Pickering Castle
FireplaceGardenBarbecue
  • 5-star holiday home with fireplace
  • Private garden and barbecue
  • Pet-friendly holiday home
From£ 158 /nightSelect
9.5
Perfect16 total reviews
our site & Booking.com
Map
8.2 km from City Centre
Private ParkingOutdoor DiningPet Friendly
  • Private garden with outdoor dining
  • Pet-friendly whole cottage rental
  • Cycling and hiking from doorstep
From£ 160 /nightSelect
Bramwood CottagesHoliday home
8.5
Great64 total reviews
our site & Booking.com
4 adults
1 bedroom
2 beds
Map
600 m from City Centre300 m from Green Man Gallery
FireplaceFull KitchenPrivate Garden
  • Self-catering cottages with fireplaces
  • Private entrance and garden
  • Fully equipped kitchen with dishwasher
From£ 165 /nightSelect
8.9
Great82 total reviews
our site & Booking.com
Map
800 m from City Centre600 m from Green Man Gallery
Garden PatioBarbecue GrillBaby Gate
  • Grade II listed period stone cottage
  • Baby safety gate for families
  • Barbecue facilities and outdoor dining
From£ 148 /nightSelect
Hallgarth HouseHoliday home
10.0
Perfect1 total review
our site & Booking.com
10 adults
5 bedrooms
5 beds
Map
600 m from City Centre300 m from Green Man Gallery
Private GardenBarbecue GrillFull Kitchen
  • 5-bedroom holiday home with garden
  • Steps from North York Moors Railway
  • Multilingual staff in 11 languages
From£ 172 /nightSelect
Grove House LevishamHoliday home
9.0
Perfect23 total reviews
our site & Booking.com
Map
7.4 km from City Centre
FireplacePrivate PatioGarden
  • Fireplace in every holiday home
  • Baby safety gate for families
  • Cycling and hiking from doorstep
From£ 87 /nightSelect
Castlegate CottageHoliday home
9.0
Perfect60 total reviews
our site & Booking.com
Map
400 m from City Centre200 m from Pickering Railway Station
Fully-equipped kitchenFireplaceBaby safety gate
  • Holiday home with private patio
  • Baby safety gate provided
  • Pets allowed on request
From£ 163 /nightSelect
8.1
Great28 total reviews
our site & Booking.com
Map
1.9 km from City Centre900 m from steam rally
Free ParkingFlat-screen TVPets Allowed
  • Steps from Flamingo Land Theme Park
  • Pet-friendly two-bedroom lodge
  • Private balcony with each unit
From£ 225 /nightSelect
9.5
Perfect39 total reviews
our site & Booking.com
2 adults
1 bedroom
1 bed
Map
7.6 km from City Centre
KitchenettesSun TerraceBicycle Parking
  • Historic farm building
  • Self-catering studios with kitchenettes
  • On-site cycling and hiking
From£ 134 /nightSelect
1 Rosedale AbbeyHoliday home
5.0
Needs improvement1 total review
our site & Booking.com
Map
13.8 km from City Centre
Private GardenFireplaceWashing Machine
  • On-site cycling, fishing & golf
  • Private garden with fireplace
  • Two-bedroom self-catering home
From£ 157 /nightSelect
Middlehead CottagesHoliday home
9.6
Perfect189 total reviews
our site & Booking.com
5 adults
3 bedrooms
3 beds
Map
8.7 km from City Centre
Private Hot TubEV ChargingFishing
  • In-unit private hot tub
  • Private electric vehicle charging
  • Picnic area with garden views
From£ 168 /nightSelect
Lark CottageHoliday home
9.3
Perfect196 total reviews
our site & Booking.com
4 adults
2 bedrooms
2 beds
Map
500 m from City Centre300 m from Green Man Gallery
Pets AllowedFireplaceFull Kitchen
  • Pet-friendly holiday home
  • Features a cozy fireplace
  • 6.9 km from Flamingo Land
From£ 81 /nightSelect
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Pickering holiday homes range from cosy cottages in the town centre to spacious lodges set in open countryside. Budget around £80-£200 per night depending on the season and property size. For easy access to the North York Moors Railway, consider staying near the station; for a quieter base, look at Levisham or the edge of Dalby Forest. Most homes include a fully equipped kitchen, free WiFi and private parking - some even have a fireplace or a hot tub.

Top-rated options include Barker Stakes Farm, a family-run 18th-century farmhouse on 16 acres with pet-friendly lodges, and Low Costa Mill, which has an indoor swimming pool and children's playground. Potter Hill Cottage sits a 5-minute walk from the railway and is ideal for exploring English Heritage sites. Grove House Levisham offers a garden and sun terrace near Dalby Forest, while Hogwarts Cottage provides a budget-friendly base with a fully equipped kitchen. Book early for summer weekends - the best properties get reserved quickly.