
Family-friendly vacation rentals in Pickering
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Pickering

Total vacation rentals
Explore 130 vacation rentals in Pickering

Nightly prices starting at
Pickering vacation rentals start at G$12,553 GYD per night before taxes and fees

Verified guest reviews
Over 4,050 verified reviews to help you choose

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
130 of Pickering vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pickering rentals

4.9 Average rating
Pickering stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Pickering
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Mill Cottage Is A Beautiful Cosy Country Escape
Escape to the country to the beautiful Moors Market town of Pickering.Just a short stroll from the centre of town lies Mill Cottage.A traditional country cottage furnished to the highest standard with a modern twist. With direct access to some of the most outstanding walks in the Moors but a fantastic convenient location for the amazing selection of country pubs , restaurants and attractions Pickering has to offer. The greatest care is taken to ensure your stay with us is as perfect as possible
Indoor spacesKitchenDecor
4.96 out of 5 average rating, 146 reviews
Country Cottage with Steam Railway Views.
Positioned on a pedestrian road, wake up to the sound of birds or the steam railway. Cosy up to the log burner or sit out in the evening sun, on our west facing decking overlooking the railway. 1 minute walk to forest paths and Pickering castle, or a 2 minute walk to the town centre; you couldn’t be more perfectly located. Pickering has the charm of a rural North Yorkshire town with all the amenities you need for a relaxing break or a family centred vacation. Discounts for stays over 2 nights.
FamilyIndoor spacesView
4.88 out of 5 average rating, 164 reviews
Stationmaster's Cottage
A detached Victorian stone cottage in the shadow of Pickering Castle and overlooking North York Moors Railway station, this characterful property with real fire is only 3 minutes walk away from town centre amenities, the castle and a ten minute walk to the start of the Tabular Hills way and gateway to the North York Moors National Park. Free parking is provided in the Platform 3 Car Park diagonally opposite the property 70 yards away (dashboard pass provided). Please note: steep stepped access.
FamilyKitchenParking
4.97 out of 5 average rating, 149 reviews
Cosy character cottage in heart of Pickering
31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, steam railway, the coast and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.
KitchenIndoor spacesSleep quality
4.92 out of 5 average rating, 390 reviews
Spacious character historic cottage
Our 17th Century, characterful Yorkshire longhouse provides a spacious, retreat, and a fantastic base for family and friends to meet up with plenty of opportunities for days out in the surrounding North York Moors. The house is in the vibrant market town of Pickering with it's famous heritage railway. Pickering has a cafes, restaurants and pubs along it's bustling high street and a weekly market selling fresh, local produce. 7+2 guests (sofa bed in the snug for 2 guests at an extra charge)
KitchenFamilyTV
4.95 out of 5 average rating, 141 reviews
Lovely cottage for N. York Moors & Steam Trains
19 Burgate is in the popular market town of Pickering, minutes’ walk from shops, eating places, Castle & Steam Railway (seasonal) - ideal for exploring the Moors, coastline & historic sights. It offers contemporary comfort, with a cosy living room, modern kitchen-diner, luxurious bathroom (walk-in shower, bath) & quality bedrooms. The garden offers eating/drinks outside and access to private parking. Prices are for 2 guests, with a small extra charge for the 2nd bedroom and well-behaved pets.
KitchenIndoor spacesHospitality
4.94 out of 5 average rating, 165 reviews
Katiann's Cottage
Accommodation Master Bedroom, en-suite walk in shower, 1 x King Size Bed, Freeview TV Twin Bedroom - 2 single beds TV Travel cot & highchair available Bedlinen & Towels Bathroom - bath, shower, sink, toilet Kitchen Diner - dishwasher, Washer, electric oven & hob, fridge, microwave, cook utensils & iron Cosy lounge 2 leather recliner sofas, Smart TV, electric log burner Gas Central Heating Free Wi-fi 1 private parking space & plenty of free public parking & chargers nearby 1 x small dog fee
FamilyIndoor spacesAccuracy
4.98 out of 5 average rating, 192 reviews
La Fenetre Holiday Cottage
Central location just one minute walk from the town centre with lots of shops, bars & restaurants. HOT TUB! Pet Friendly. Contact us for special offers. Private outdoor courtyard. Our cottage offers very comfortable accommodation and is within easy walking distance of amenities, parking very close by, the perfect base for exploring local attractions, including York, Whitby, Scarborough, Dalby Forest, Flamingo Land & North Yorkshire Moors. The cottage is snug & makes maximum use of space.
FamilyKitchenWalkability
4.81 out of 5 average rating, 535 reviews
Castlegate Cottage
Characterful and quaint 3 bedroom Grade II listed cottage, built in 1800 with open plan living. Within easy walking distance of many shops, tea rooms, restaurants, pubs and the castle, there is parking very close by. Castlegate cottage is a perfect base for exploring the many local attractions and places of interest, such as The Steam railway, Beck Isle museum, The North Yorkshire Moors, Whitby, Scarborough, Flamingo Land, Eden Camp, Dalby Forest and York.
Indoor spacesFamilySleep quality
4.93 out of 5 average rating, 420 reviews
2 bed Cottage Pickering, Priv Parking, Logburner
Oak Cottage is in the perfect place to explore Pickering and the surrounding North Yorkshire Moors and Coast. With Parking for 1 car and Just a 5 to 10 minute walk into central Pickering and the NYM Railway. Fully equipped for a comfortable and relaxing stay with lots of luxurious extras. We can sleep upto 4 people and one well behaved dog is welcome, but must be added to your booking for a small charge. It is a terraced cottage on the main road.
FamilyKitchenSleep quality
4.95 out of 5 average rating, 130 reviews
Stunning views, 4 acres, dog friendly, Yorkshire
Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.
Indoor spacesKitchenHiking
4.94 out of 5 average rating, 386 reviews
Lovely Cottage & Garden. Family & Bike Friendly
A stunning 3 bedroom cottage & garden in Thornton. Family & MTB/cyclist friendly. A converted period building in the beautiful North York Moors National Park, ideal as a base for your outdoor activities or quiet getaway in this famously picturesque Yorkshire village. Beautifully light and spacious stone cottage with period features and all modern facilities. Set in the quiet Prospect Place cul-de-sac with your own off-street parking space.
KitchenIndoor spacesGrill
4.94 out of 5 average rating, 143 reviewsPopular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

Dalby Forest Luxury Lodge
FamilyIndoor spacesHot tub
4.98 out of 5 average rating, 121 reviews
3 Railway Cottage Pickering, Hot-Tub, Pets.
FamilyKitchenCleanliness
4.9 out of 5 average rating, 197 reviews
Charming farm based cottage with hot tub/sauna
KitchenIndoor spacesParking
4.97 out of 5 average rating, 236 reviews
2 bedroom lodge with hot tub in private woodland
FamilyKitchenCheckout
4.94 out of 5 average rating, 170 reviews
Langton Hall - Grade 2 listed
FamilyKitchenGetting around
4.94 out of 5 average rating, 198 reviews
Moo view Luxury Shepherd’s hut
FamilyIndoor spacesHot tub
4.94 out of 5 average rating, 171 reviews
Wykeham Cottage, Stunning Cottage in Harwood Dale
KitchenIndoor spacesAccuracy
4.96 out of 5 average rating, 195 reviews
Luxury Country Cottage Hot Tub Spa Retreat | York
KitchenIndoor spacesCleanliness
4.98 out of 5 average rating, 129 reviewsFamily- and pet-friendly home rentals

Yorkshire cottage with private parking &EV charger
Indoor spacesKitchenWalkability
4.98 out of 5 average rating, 116 reviews
Between Coast & Moors • Pickering 2BR • Sleeps 4
KitchenIndoor spacesParking
4.84 out of 5 average rating, 145 reviews
The Town House
FamilyKitchenCleanliness
4.93 out of 5 average rating, 104 reviews
Renovated 16th century haven in North Yorks Moors
KitchenFamilyAccuracy
4.89 out of 5 average rating, 227 reviews
Highfield Annex with off St Parking in Keldholme
Indoor spacesFamilyDecor
4.99 out of 5 average rating, 120 reviews
Goose End Cottage, North Yorkshire
FamilyIndoor spacesBathroom
4.97 out of 5 average rating, 158 reviews
Forest View Lodge
FamilyIndoor spacesHiking
4.97 out of 5 average rating, 126 reviews
Oakforge Cottage, a spacious home from home.w
KitchenIndoor spacesWifi
4.9 out of 5 average rating, 478 reviewsFamily-friendly home rentals with a pool

Ellerburn Lodge
Indoor spacesKitchenView
4.87 out of 5 average rating, 244 reviews
Cosy 2 bedroom river/coastal retreat. Heated pool.
FamilyIndoor spacesTV
4.79 out of 5 average rating, 137 reviews
Secret of Eden Beach House - Pet friendly WiFi E.V
FamilyIndoor spacesLocation
4.97 out of 5 average rating, 445 reviews
3 bedroom cottage with fabulous sea views.
KitchenIndoor spacesGrill
4.86 out of 5 average rating, 104 reviews
Willow Cottage: 3 Bed, 3 Bath, Pool, WiFi, dogs
KitchenFamilyComfort
4.97 out of 5 average rating, 133 reviews
Meadowside House, The Bay Filey (Sleeps up to 9)
KitchenFamilyBeach
4.97 out of 5 average rating, 130 reviews
Relax at lovely Collie Cottage, The Bay Filey
KitchenIndoor spacesCondition
4.99 out of 5 average rating, 212 reviews
Salty Kisses, The Bay, Filey
KitchenFamilyPool
4.92 out of 5 average rating, 168 reviewsWhen is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$36,614 GYD | G$38,287 GYD | G$37,032 GYD | G$39,124 GYD | G$39,752 GYD | G$40,380 GYD | G$40,380 GYD | G$39,543 GYD | G$36,823 GYD | G$36,614 GYD | G$37,241 GYD | G$40,589 GYD |
| Avg. temp | 3°C | 3°C | 5°C | 7°C | 10°C | 12°C | 15°C | 14°C | 12°C | 9°C | 6°C | 3°C |
Destinations to explore
- Yorkshire Coast
- Flamingo Land Resort
- Filey Beach
- Durham Cathedral
- Fountains Abbey
- Harewood House
- Bempton Cliffs
- York Castle Museum
- Bramham Park
- Scarborough Open Air Theatre
- York University
- Temple Newsam Park
- York Minster
- Scarborough Beach
- National Railway Museum
- Teesside University
- The Deep
- Peasholm Park
- Bridlington Spa
- Durham University
- First Direct Arena
- Saltburn Beach
- Kynren
- Blue Dolphin Holiday Park - Haven





