Vacation rentals in Pickering

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pickering

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
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, 137 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

Guest favorite
The kitchen area is designed with a wood countertop and light cabinetry. A sink is located beside a window that allows natural light to illuminate the space. Fresh greenery is positioned on the sill, and neatly arranged utensils and containers enhance the organized ambiance.
Cottage in Pickering
4.83 out of 5 average rating, 310 reviews

Cosy ‘Cobblers Cottage’ - Pickering

Enjoy easy access to everything from our perfectly located, traditional stone home on the gateway to the North York Moors National Park. Just steps away from Pickering town centre with an array of shops, pubs, cafes, bars, restaurants, bakers, butchers & takeaways on offer. A short stroll to the North Yorkshire Moors Railway giving pleasant & easy access to Whitby, Goathland, Levisham, Newtondale and Grosmont. Also perfectly located for Scarborough, Whitby, Malton, Helmsley & Dalby Forrest.

Top guest favorite
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 Pickering
4.91 out of 5 average rating, 356 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 favorite
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 Pickering
4.97 out of 5 average rating, 118 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 favorite
Condo in Malton
4.98 out of 5 average rating, 303 reviews

Luxury boutique apartment-2 Chiltern Place Malton

Relax in this luxury boutique apartment located within a stylish, distinctive merchants building in the heart of Malton. New soft furnishings for 2025. Accommodation comprises of: entrance hall, guest cloakroom, utility room, open plan living area with contemporary inset fire, high specification kitchen & dining area. Master bedroom suite, king bed, luxury en-suite & private terrace. WiFi & underfloor heating. Free private parking on the property and space for 2 bikes in the storage area.

Top guest favorite
The exterior of a characterful Yorkshire longhouse is displayed, showcasing stone walls and a tiled roof. Flower baskets hang from the front, adding a touch of color. The entrance features a light-colored door framed by two potted plants. Windows reflect a welcoming ambiance.
Cottage in Pickering
4.96 out of 5 average rating, 125 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)

Top guest favorite
A charming cottage exterior is surrounded by lush greenery, featuring a stone facade and a blue front door. Tall trees and neatly trimmed bushes frame the entrance, while wildflowers and grass add a natural touch to the pathway. The peaceful setting invites exploration.
Cottage in Pickering
4.84 out of 5 average rating, 197 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 favorite
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 Pickering
4.93 out of 5 average rating, 361 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/

Superhost
An outdoor courtyard is presented with a hot tub, framed by greenery and stone walls. A wooden table holding a teapot and cups adds a cozy touch. Decorative elements like pinecones and flowers enhance the space, inviting relaxation in this private setting.
Cottage in Pickering
4.82 out of 5 average rating, 504 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.

Top guest favorite
The exterior showcases a charming stone cottage with large windows, allowing natural light to fill the interior. A gated entrance leads to a gravel path, framed by a low stone wall and greenery, offering a tranquil setting in a quiet area.
Cottage in Pickering
4.98 out of 5 average rating, 171 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, Ninja Air Fryer, 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 car parking public chargers nearby 1 x small dog subject to fee

Guest favorite
A view of tranquil rooftops showcasing the unique character of the surrounding buildings with a mix of red brick and tile. Lush greenery and trees provide a soft backdrop, highlighting the natural beauty found in this serene rural area.
Home in Pickering
4.89 out of 5 average rating, 143 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 favorite
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 Pickering
4.93 out of 5 average rating, 391 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.

Popular amenities for Pickering vacation rentals

When is the best time to visit Pickering?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$29,719 GYDG$29,091 GYDG$29,091 GYDG$32,440 GYDG$33,486 GYDG$34,323 GYDG$35,160 GYDG$34,742 GYDG$34,114 GYDG$34,323 GYDG$31,603 GYDG$36,625 GYD
Avg. temp3°C3°C5°C7°C10°C12°C15°C14°C12°C9°C6°C3°C

Frequently Asked Questions

  • How much does it cost to stay in cottage rentals in Pickering?

    Experience the best of Pickering with our cottage rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there cottage rentals with a dedicated workspace in Pickering?

    Yes! Work meets play with ease at over 30 cottage rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly house rentals in Pickering?

    Four-legged friends are welcome in Pickering. Choose from more than 20 house rentals for guests traveling with pets.

  • Do house rentals in Pickering have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Pickering have wifi?

    Absolutely! We offer over 70 cottage rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pickering have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Pickering?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 40 homes with wifi, over 40 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly cabin rentals in Pickering?

    Pickering has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Pickering

  • Total vacation rentals

    Explore 150 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at G$12,557 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,200 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    150 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!

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