Holiday rentals in Pickering

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Top-rated holiday rentals in Pickering

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Guest favourite
A traditional stone cottage features a charming entryway adorned with climbing plants. A small outdoor seating area, furnished with a round table and decorative chairs, provides a pleasant space for relaxation. The roof is covered with terracotta tiles, complementing the natural stone exterior.
Cottage in Pickering
4.96 out of 5 average rating, 138 reviews

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

Top guest favourite
The cottage is constructed of traditional stone, showcasing a quaint exterior with a pitched roof and chimney. Two large windows with flower boxes frame the entrance, which features a light-colored door. The surroundings include a peaceful street lined with other characterful buildings.
Cottage in North Yorkshire
4.91 out of 5 average rating, 362 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.

Top guest favourite
A charming Victorian stone cottage stands against a backdrop of greenery. The cottage features a mix of dark stone and light brick, with a small front porch and a sloped garden area. Two large windows allow natural light to enter the welcoming interior.
Home in North Yorkshire
4.98 out of 5 average rating, 123 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.

Top guest favourite
The exterior of a charming stone cottage is visible, featuring a traditional roof with red tiles. Two entrances can be seen, framed by multiple windows that allow natural light to enter. The facade combines a rustic aesthetic with neighborhood characteristics.
Cottage in North Yorkshire
4.93 out of 5 average rating, 152 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.

Top guest favourite
A snug lounge area is shown with a sofa adorned with colorful cushions, a wooden TV stand below a flat-screen television, and soft lighting creating a welcoming ambiance. Stairs lead to an upper level, accompanied by decorative elements on the walls.
Cottage in North Yorkshire
4.84 out of 5 average rating, 202 reviews

Cosy one bedroom cottage in Pickering

This lovely cottage is nestled in the centre of the beautiful market town of Pickering, Relax at this charming cottage which offers easy access to the enchanting landscapes of the North Yorkshire Moors and the nearby towns and coast. Whether you visit the iconic North Yorkshire Moors Railway, attend a concert at the Scarborough Open Air Theatre, or spend a day at the beach or exploring Whitby and the Moors. If you are seeking relaxation or adventure, this unique getaway is the perfect choice.

Top guest favourite
A detached holiday cottage features a red front door and distinctive round window, set against a backdrop of textured brick walls. The surrounding area is landscaped with greenery, and gravel provides off-road parking in front of the building.
Cottage in North Yorkshire
4.93 out of 5 average rating, 368 reviews

APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE

Detached holiday cottage Sleeps two (ONE DOUBLE BED) FREE WIFI Off road parking En-suite bathroom Fully equipped kitchen TV and fridge freezer Microwave Ideal location for all local attractions 2 minute walk into Pickering and local pubs, restaurants and shops Quotes from past guests: it's just perfect/best cottage we've stayed in/everything is so welcoming/ location is fantastic Places to visit in North Yorkshire http://www.iknow-yorkshire.co.uk/attractions/north_yorkshire/

Top guest favourite
Cottage in North Yorkshire
4.98 out of 5 average rating, 174 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

Top guest favourite
A steam train is seen departing from a vintage railway station, with wisps of steam billowing from the engine. The station's platform is surrounded by greenery, and classic signal lights are positioned along the tracks, enhancing the historical ambiance.
Home in North Yorkshire
4.88 out of 5 average rating, 226 reviews

Short stroll to pubs, cafés & shops. Free Parking

Enjoy a clean and comfortable, cosy yet spacious, experience at this peacefully located holiday home. Just a very short stroll from Pickering town centre where you’ll be spoilt for choice with a whole host of shops, cafes, bars, pubs and restaurants. Offering a stylish, comfortable space with all you need. Ideal as a base to enjoy and explore all great North Yorkshire has to offer. Free on street parking or free parking permit for Eastgate car park which is less than 300 meters away.

Superhost
Home in North Yorkshire
4.88 out of 5 average rating, 147 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. A 1 minute walk to forest walks 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.

Top guest favourite
The exterior of the cottage displays a charming stone facade with a red-tiled roof. A large window with multiple panes is positioned at the front, while two dormer windows are set into the roof, providing additional natural light to the upper levels.
Cottage in North Yorkshire
4.93 out of 5 average rating, 397 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.

Top guest favourite
The open plan living area features a log burner surrounded by a brick fireplace, complemented by a comfortable blue chair and a coffee table. A dining area with a wooden table is visible in the background, while a fully equipped kitchen is accessed through an archway.
Cottage in North Yorkshire
4.95 out of 5 average rating, 117 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.

Guest favourite
A large floor-to-ceiling window offers expansive views of the countryside and sunlight filtering through trees. A warm wooden bench is adorned with a welcoming sign and small plants. A cozy coffee table with decorative items can be seen in front, enhancing the inviting space.
Barn in Aislaby, Pickering
4.95 out of 5 average rating, 358 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.

Popular amenities for Pickering holiday rentals

When is the best time to visit Pickering?

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Avg. price$193 SGD$198 SGD$196 SGD$196 SGD$203 SGD$208 SGD$213 SGD$210 SGD$207 SGD$208 SGD$191 SGD$222 SGD
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Frequently Asked Questions

  • What are the best places to stay in Pickering?

    The town center area has character guesthouses, traditional cottages, and modern apartments, making it convenient for exploring markets, eateries, and historical sites on foot. Rural surroundings also include converted barns and countryside retreats for a quieter stay.

  • What are the best things to do in Pickering with kids?

    Kids often enjoy exploring Pickering Castle, boarding the North Yorkshire Moors Railway for a steam train adventure, or playing in riverside parks. Farm visits and craft workshops are other frequently suggested options.

  • What are some of the best things to do in Pickering?

    Explore Pickering Castle, ride the North Yorkshire Moors Railway, and visit the Beck Isle Museum for local heritage. Browsing markets, independent shops, and riverside walks reveals the area's character.

  • How is the weather in Pickering?

    Pickering has cool, damp winters with highs near 41–46°F (5–8°C) and milder summers averaging 60–66°F (16–19°C). Waterproofs and layers are useful year-round, as rain is common across seasons.

  • When is the best time to visit Pickering?

    Late spring through early autumn is often recommended for milder weather and seasonal events. Some visitors enjoy winter for quieter towns and festive markets, but packing for cooler temperatures around 33–42°F (1–6°C) is helpful.

  • What are the best places to visit in Pickering?

    The most popular sites include Pickering Castle, the parish church with medieval wall paintings, and the North Yorkshire Moors Railway. Many guests also explore nearby forests and heather-clad moors.

  • What are some hiking trails in Pickering?

    Explore woodland paths in Cropton Forest, gentle walks along Pickering Beck, or venture toward nearby moorland trails. These routes often feature scenic views and glimpses of local wildlife.

  • What are some family activities we can do in Pickering?

    Families often explore Pickering Castle, join a steam train ride on the heritage railway, or enjoy interactive exhibits at local museums. Green spaces and adventure play areas also create opportunities for outdoor fun.

  • What are some of the best day trip ideas from Pickering?

    Explore the historic city of York, beaches around the Yorkshire coast, or charming moorland villages known for walking and traditional markets. Nearby castles and ruins add to the variety of day excursions.

  • Are there any pet friendly accommodations available in Pickering?

    Many accommodations in Pickering's countryside and town center welcome pets, especially in cottages, farm stays, and select apartments. Walking trails and pet-friendly cafes around Pickering make it easy to include pets in your plans.

  • What are some local tips for visiting Pickering?

    Locals often suggest exploring smaller side streets for independent shops and sampling a traditional Yorkshire afternoon tea. Arriving early for market days or railway journeys can help you enjoy a quieter experience.

  • What is Pickering known for?

    Pickering is known for its historic castle, heritage railway, and as a gateway to the North York Moors National Park. The town has roots in medieval history, markets, and railway traditions.

  • What are the best hidden gems to explore in Pickering?

    Pickering has lesser-known corners, such as small local galleries, quiet riverside trails, and village tearooms with distinct character. Exploring independent antique shops and the town's market days unveils local traditions and crafts.

  • What are the best foods to try in Pickering?

    Pickering has traditional Yorkshire treats such as pork pies, Wensleydale cheese, and hearty meat and vegetable pies. Seasonal cakes and local ales are often enjoyed in cafes and pubs around the town.

  • What should I bring for a trip to Pickering?

    Bring layered clothing for shifting temperatures, waterproofs for rain, and comfortable walking shoes for uneven terrain. A camera helps capture the medieval architecture, steam trains, and moorland scenery.

  • What is the nightlife in Pickering like?

    Pickering has a relaxed nightlife scene centered around traditional pubs, quiet lounges, and occasional live music in local inns. Most evenings are low-key, creating a welcoming atmosphere for conversation and sampling local ales.

  • What are the most popular events or festivals in Pickering?

    Pickering hosts events like the wartime-themed 1940s Weekend, vintage car rallies, and seasonal fairs celebrating local traditions. Folk and craft festivals are also frequently suggested by residents and visitors.

  • Are there family friendly vacation rentals in Pickering?

    Pickering's holiday cottages, barn conversions, and town center apartments frequently welcome families. Many rentals have amenities such as kitchens and enclosed gardens to support family needs during your stay.

Quick stats about holiday rentals in Pickering

  • Total holiday rentals

    Explore 150 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    150 of Pickering holiday rentals include wifi 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!

  1. Airbnb
  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Pickering