Photo by Ian Hall

Winston holiday homes

We found 492 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Winston that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, such as parking and air conditioning. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Find the best place to stay - Winston

ROSE COTTAGE, family friendly, character holiday cottage in Winston

Sleeps 4 · 2 bedrooms · 1 bathroom

ELLABERRY, family friendly, with open fire in Ingleton, County Durham

Sleeps 6 · 3 bedrooms · 2 bathrooms

1 Springwater View, Mickleton, Teesdale

Sleeps 8 · 4 bedrooms · 3 bathrooms

2 bedroom accommodation in Staindrop, near Barnard Castle

Sleeps 4 · 2 bedrooms · 1 bathroom

PEACE COTTAGE, pet friendly, character holiday cottage in Langton

Sleeps 6 · 3 bedrooms · 2 bathrooms

3 bedroom accommodation in Boldron, near Barnard Castle

Sleeps 7 · 3 bedrooms · 2 bathrooms

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Why visit Winston

Heritage charm: Discover the quaint history of Winston through its picturesque Witton Castle and charming local landmarks.
Family-friendly fun: Enjoy a range of activities suitable for visitors of all ages, including leisurely strolls and adventurous outings.
Natural beauty: Revel in the serene ambience provided by nearby waterfalls and outdoor spaces perfect for relaxation.
Cultural experiences: Immerse yourself in the local heritage and community spirit that gives Winston its unique character.
Leisure and romance: Unwind at local leisure centres and enjoy the peaceful, inviting atmosphere ideal for a memorable holiday.

Top attractions near Winston

Winston, located in Darlington, England, offers a delightful mix of family-friendly activities and stunning outdoor experiences. Visitors can explore the picturesque Witton Castle and enjoy the serene beauty of local waterfalls. The area is ideal for those seeking culture and romance, with leisure centres providing entertainment for all ages. Whether you're wanting a leisurely stroll or an adventurous day out, Winston has something to cater to every traveller's needs.

Barnard Castle: A romantic, culturally rich castle located 10km away, offering historical charm and scenic surroundings.
Croft Circuit: A thrilling motor racing venue 18km away, providing sports and adventure experiences for enthusiasts.
Eggleston Hall: A historic house 16km away, exuding cultural allure and timeless elegance.

Things to do recommended for couples

Discover the charm of Winston, Darlington, with a leisurely walk along the River Tees or enjoy a cosy picnic at the picturesque Hall Garth Park. For a touch of magic, indulge in a romantic dinner at a local bistro, savouring delicious dishes together under a starlit sky.

Things to do recommended for families

In Winston, families can explore local parks, visit heritage sites, and enjoy child-friendly activities, ensuring a memorable holiday experience in Darlington. Discover outdoor adventures and cultural sites suitable for all ages in this charming locale.

Things to do recommended for groups

Groups visiting Winston can experience the thrill of motor racing at Croft Circuit, located 18km away. This exciting venue offers a blend of sports and adventure, perfect for those looking to enjoy high-speed action and camaraderie in a vibrant atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winston

If you're travelling with a group, family, pets, or planning for an extended stay, it's important to use the right filters to match your priorities. Here are some helpful Vrbo booking tips for you.

Traveling to Winston with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
Traveling to Winston with young kids: Traveling with little ones can be demanding. You must ensure their well-being and security, along with age-suitable features like a private swimming pool. It’s also wise to consider how close you are to attractions that cater to families.
Taking your pets with you to Winston: For many, a family holiday isn’t the same without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Winston: If you’re after holiday rentals with special rates for month-long stays, you’ve come to the right spot. With the correct filter, you can effortlessly locate and save on monthly rentals. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Winston

Winston, Darlington offers a delightful mix of family-friendly and outdoor experiences. Discover its charming atmosphere, rich culture, and relaxing luxury. Explore local landmarks and enjoy the welcoming community spirit, all within this quaint village. Ideal for a memorable holiday in a peaceful setting, Winston invites travellers to immerse in its unique blend of heritage and modern leisure.

Staindrop: A charming village located 5km away from Winston, Staindrop invites travellers with a culture-themed, romantic, and scenic experience. The village is a gateway to educational and recreational areas with nearby landmarks including a castle, national park, and national state park. Whether you’re exploring the historic streets or enjoying the natural beauty of the surrounding countryside, Staindrop offers a relaxed yet enriching escape for those keen on history and nature.
Richmond: Set 16km from Winston, Richmond is a vibrant city that promises an outdoor, adventure, and scenic experience. With its proximity to expansive national parks and a majestic castle, the city is ideal for visitors who love exploring nature and engaging in outdoor activities. Richmond is also known for its recreational areas and opportunities for body treatments, providing a diverse range of experiences for active holidaymakers and those seeking to unwind.
Barnard Castle: Located 10km from Winston, Barnard Castle is a city that offers an enticing blend of outdoor adventure and scenic beauty. It is surrounded by expansive natural settings including a national park, national state park, and a historic castle. With recreational areas and wellness activities like spa and body treatments, Barnard Castle is well-suited for visitors seeking both excitement and relaxation in a picturesque environment.

Best time to go to Winston

If you're planning a trip to Winston, it's a good idea to check both the weather and property rates. The warmest month is July.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	37.2°F (2.9°C)	Light Rain	Mostly Cloudy
February	38.5°F (3.6°C)	Light Rain	Mostly Cloudy
March	41.0°F (5.0°C)	Light Rain	Mostly Cloudy
April	44.8°F (7.1°C)	No Rain (Dry)	Mostly Cloudy
May	50.0°F (10.0°C)	Light Rain	Mostly Cloudy
June	55.6°F (13.1°C)	Light Rain	Mostly Cloudy
July	59.0°F (15.0°C)	Light Rain	Mostly Cloudy
August	58.3°F (14.6°C)	Light Rain	Mostly Cloudy
September	54.5°F (12.5°C)	Light Rain	Mostly Cloudy
October	49.3°F (9.6°C)	Light Rain	Mostly Cloudy
November	43.0°F (6.1°C)	Light Rain	Mostly Cloudy
December	38.7°F (3.7°C)	Light Rain	Mostly Cloudy

Booking with Vrbo is simple

Looking to stretch your travel dollars? Being flexible with your travel dates can help you take advantage of fluctuating prices. And by opting for an extended stay, you can often unlock significant savings. Use our handy filters to sort by price, location, and type of holiday rental to find the perfect Vrbo property for your budget.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy space where you can create new trips, continue planning where you stopped, or review and organise your travel plans. You’ll see your saved or booked properties sorted into Potential, Upcoming, or Current Trips. To start using Trip Boards, visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Winston getaway

Learn about the unique charm of Winston with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Winston

Are you hoping to find things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winston a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Rockliffe Hotel Spa (10.7 mi / 17.2 km)
Croft Circuit (11.2 mi / 18.1 km)
The Garage Spa (4 mi / 6.4 km)
Walworth Castle Birds of Prey (5.7 mi / 9.3 km)
Brancepeth Castle Golf Club (14.2 mi / 22.8 km)
Heritage Park Stadium (7.4 mi / 11.9 km)

Exploring the natural features in Winston

Whether you're looking for adventure or just want to appreciate the scenery, Winston is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

Yorkshire Dales National Park (22 mi / 35.4 km)
Hamsterley Forest (9.4 mi / 15.1 km)
Whitworth Hall Country Park (12.8 mi / 20.7 km)
Wynyard Woodland Park (16.9 mi / 27.3 km)
High Force (17.7 mi / 28.4 km)
Wensleydale (20.9 mi / 33.7 km)

How to get to and around Winston

Fly into Durham (MME-Teesside Intl.), the closest airport, located 14.3 mi (23 km) from the city centre.

Frequently asked questions

What is the best area to stay in Winston when booking a holiday rental?

When considering a holiday rental in Winston, England, a popular area to stay is the charming village itself, known for its picturesque landscapes and welcoming atmosphere. This quaint location offers a range of properties that cater to various preferences, from cosy cottages to larger family homes. Staying in Winston allows you easy access to the stunning surrounding countryside, great for leisurely walks and enjoying nature.A short distance from Winston, you can explore the remarkable local attractions, such as the historic village church, which showcases beautiful architecture and a fascinating history. Additionally, the nearby nature reserves offer wonderful opportunities for bird watching and enjoying the great outdoors. The area has a selection of holiday rentals available, providing visitors with a delightful base to explore the enchanting surroundings and experience the local culture.

What are the top attractions in Winston?

Winston, a quaint village in England, offers a charming experience with several attractions nearby. The picturesque countryside is superb for leisurely walks and exploring nature, with scenic routes that showcase the area's beauty. The village itself features traditional architecture and a few local shops and cafes that provide a taste of local life.A short drive away, visitors can explore the historic market town of Richmond, known for its stunning views of the River Swale and the impressive Richmond Castle, which dates back to the 11th century. The beautiful landscapes of the Yorkshire Dales National Park are also within reach, providing opportunities for hiking, cycling, and enjoying the breathtaking scenery.Additionally, the nearby town of Leyburn offers a variety of independent shops and is close to attractions such as the Bolton Castle, a well-preserved medieval fortress. For those interested in history and culture, the Dales Countryside Museum in Hawes provides insights into the local heritage and environment.

Are all fees included in the Winston holiday homes prices shown on Bookabach?

Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

Are there any Winston holiday homes with parking?

Bookabach offers a wide selection of holiday homes in Winston with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

Are there any discounts for Winston holiday homes?

You can find great discounts on holiday homes in Winston on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I change or cancel my Winston holiday home booking on Bookabach?

To find Winston holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.

Can I find long-stay holiday homes in Winston?

A long-stay holiday home in Winston is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Can I plan a group trip on Bookabach?

Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.

How early should I book a Winston holiday home?

Book your Winston holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.

How much does it cost to rent a holiday home in Winston?

Prices for holiday homes in Winston vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Winston to more spacious homes.

What can I expect from Bookabach customer service and Bookabach Care™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

What is Bookabach Care™ and how does it work?

Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

Why should I join Bookabach as a host?

Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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